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more..
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77950552502
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Pettus, L. H.; Wurz, R. P.; Xu, S.; Herberich, B.; Henkle, B.; Liu, Q.; McBride, H. J.; Mu, S.; Plant, M. H.; Saris, C. J. M.; Sherman, L.; Wong, L. M.; Chmait, S.; Lee, M. R.; Mohr, C.; Hsieh, F.; Tasker, A. S. J. Med. Chem. 2010, 53, 2973
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Mohr, C.15
Hsieh, F.16
Tasker, A.S.17
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9
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60849134008
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Achmatowicz, M.; Thiel, O. R.; Wheeler, P.; Bernard, C.; Huang, J.; Larsen, R. D.; Faul, M. M. J. Org. Chem. 2009, 74, 795
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Achmatowicz, M.1
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Wheeler, P.3
Bernard, C.4
Huang, J.5
Larsen, R.D.6
Faul, M.M.7
-
10
-
-
65949104045
-
-
Thiel, O. R.; Achmatowicz, M.; Bernard, C.; Wheeler, P.; Savarin, C.; Correll, T.; Kasparian, A.; Allgeier, A.; Bartberger, M. D.; Tan, H.; Larsen, R. D. Org. Process Res. Dev. 2009, 13, 230
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Thiel, O.R.1
Achmatowicz, M.2
Bernard, C.3
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Savarin, C.5
Correll, T.6
Kasparian, A.7
Allgeier, A.8
Bartberger, M.D.9
Tan, H.10
Larsen, R.D.11
-
12
-
-
79251515555
-
-
18 may be observed via HPLC. Isolated 18 is a crystalline solid that slowly cyclizes to 6a in the solid state
-
18 may be observed via HPLC. Isolated 18 is a crystalline solid that slowly cyclizes to 6a in the solid state.
-
-
-
-
14
-
-
0010777419
-
-
Holland, D. G.; Moore, G. J.; Tamborski, C. J. Org. Chem. 1964, 29, 3042
-
(1964)
J. Org. Chem.
, vol.29
, pp. 3042
-
-
Holland, D.G.1
Moore, G.J.2
Tamborski, C.3
-
15
-
-
79251515853
-
-
N -Acylation was also observed under the reaction conditions. N -Acylation of 5b imparted significant stabilization.
-
N -Acylation was also observed under the reaction conditions. N -Acylation of 5b imparted significant stabilization.
-
-
-
-
16
-
-
65949092920
-
-
Weidenhagen, R.; Wegner, H.; Lung, K. H.; Nordstrom, L. Chem.Ber. 1939, 72B, 2010
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(1939)
Chem.Ber.
, vol.72
, pp. 2010
-
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Weidenhagen, R.1
Wegner, H.2
Lung, K.H.3
Nordstrom, L.4
-
17
-
-
79251471209
-
-
note
-
During preparation of this manuscript, Norris et al. from Pfizer Process R&D reported a related application of the use of ascorbic acid in the reduction of diazonium salts
-
-
-
-
18
-
-
65949100625
-
-
Norris, T.; Bezze, C.; Franz, S. Z.; Stivanello, M. Org. Process Res. Dev. 2009, 13, 354
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, vol.13
, pp. 354
-
-
Norris, T.1
Bezze, C.2
Franz, S.Z.3
Stivanello, M.4
-
19
-
-
79251528647
-
-
Safety studies were carried out and showed 25 to be thermally stable under 160 °C.
-
Safety studies were carried out and showed 25 to be thermally stable under 160 °C.
-
-
-
-
20
-
-
84986533259
-
-
Acevedo, O. L.; Krawczyk, S. H.; Townsend, L. B. J. Heterocycl. Chem. 1985, 22, 349
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, vol.22
, pp. 349
-
-
Acevedo, O.L.1
Krawczyk, S.H.2
Townsend, L.B.3
-
21
-
-
79251529273
-
-
2 afforded 4% of 29a.
-
2 afforded 4% of 29a.
-
-
-
-
22
-
-
79251510958
-
-
All reactions achieved complete conversion with 19 h.
-
All reactions achieved complete conversion with 19 h.
-
-
-
-
26
-
-
0001478826
-
Hunsdiecker and Related Reactions
-
Trost. B.M.; Fleming I., Eds.; Pergamon Press: Oxford
-
Crich, D. Hunsdiecker and Related Reactions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 717 - 734.
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(1991)
Comprehensive Organic Synthesis
, vol.7
, pp. 717-734
-
-
Crich, D.1
-
27
-
-
0001570443
-
-
Graven, A.; Jorgensen, K. A.; Dhal, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543
-
(1994)
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, vol.59
, pp. 3543
-
-
Graven, A.1
Jorgensen, K.A.2
Dhal, S.3
Stanczak, A.4
-
29
-
-
20344381300
-
-
Kuang, C.; Yang, Q.; Senboku, H.; Tokuda, M. Synthesis 2005, 1319
-
(2005)
Synthesis
, pp. 1319
-
-
Kuang, C.1
Yang, Q.2
Senboku, H.3
Tokuda, M.4
-
30
-
-
79251496743
-
-
note
-
Attempts to observe 33 via react-IR failed due to its low concentration. Ionization under standard LC/MS conditions was also not successful. Related intermediates were previously observed by NMR spectroscopy in the decarboxylative bromination of cis -cinnamic acid. See ref 19b.
-
-
-
-
31
-
-
79251479805
-
-
For poorly soluble products, starting material may become entrained in the product, making it unavailable for reaction.
-
For poorly soluble products, starting material may become entrained in the product, making it unavailable for reaction.
-
-
-
-
32
-
-
33947469856
-
-
Kornblum, N.; Smiley, R. A.; Blackwood, P. K.; Iffland, D. C. J. Am. Chem. Soc. 1955, 77, 6269
-
(1955)
J. Am. Chem. Soc.
, vol.77
, pp. 6269
-
-
Kornblum, N.1
Smiley, R.A.2
Blackwood, P.K.3
Iffland, D.C.4
-
33
-
-
0000720793
-
-
Hopkins, G. G.; Jonak, J. P.; Minnemeyer, H. J.; Tieckelmann, H. J. Org. Chem. 1967, 32, 4040
-
(1967)
J. Org. Chem.
, vol.32
, pp. 4040
-
-
Hopkins, G.G.1
Jonak, J.P.2
Minnemeyer, H.J.3
Tieckelmann, H.4
-
35
-
-
79251528303
-
-
LiBr was critical to improve the N - vs O -selectivity.
-
LiBr was critical to improve the N-vs O -selectivity.
-
-
-
-
36
-
-
79251474122
-
-
note
-
4 may be considered a privileged base for large-scale Suzuki couplings of this type as it is applicable to a wide range of substrates and does not present off-gassing issues upon neutralization.
-
-
-
-
37
-
-
79251513699
-
-
The major byproducts, 36 and 37 derived from 13 via deboronation and homocoupling, respectively, and 35 derived from 10b via dehalogenation, were fully characterized and their identities confirmed by synthesis.
-
The major byproducts, 36 and 37 derived from 13 via deboronation and homocoupling, respectively, and 35 derived from 10b via dehalogenation, were fully characterized and their identities confirmed by synthesis.
-
-
-
-
38
-
-
16844367937
-
-
Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4685
-
-
Barder, T.E.1
Walker, S.D.2
Martinelli, J.R.3
Buchwald, S.L.4
-
39
-
-
3042654141
-
-
Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1871
-
-
Walker, S.D.1
Barder, T.E.2
Martinelli, J.R.3
Buchwald, S.L.4
-
40
-
-
34447307124
-
-
Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J. J. Org. Chem. 2007, 72, 5104
-
(2007)
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, vol.72
, pp. 5104
-
-
Guram, A.S.1
Wang, X.2
Bunel, E.E.3
Faul, M.M.4
Larsen, R.D.5
Martinelli, M.J.6
-
41
-
-
79251491119
-
-
Loading studies demonstrating that 0.1 mol % catalyst was sufficient to obtain both full conversion and acceptable reaction kinetics (<4 h).
-
Loading studies demonstrating that 0.1 mol % catalyst was sufficient to obtain both full conversion and acceptable reaction kinetics (<4 h).
-
-
-
-
42
-
-
79251528960
-
-
Isopropanol and water are typically miscible in all proportions; however, aqueous salt solutions are often immiscible with isopropanol.
-
Isopropanol and water are typically miscible in all proportions; however, aqueous salt solutions are often immiscible with isopropanol.
-
-
-
-
43
-
-
79251507069
-
-
note
-
The imidazolide intermediate was unstable under the HPLC conditions (0.1% TFA in acetonitrile/water); however, it could be quenched with benzylamine and then analyzed as the corresponding benzamide.
-
-
-
-
44
-
-
79251520045
-
-
note
-
The entrained imidazolide remained unreacted in isolated 4; however, it readily reacted with the solvent upon dissolution in the subsequent step.
-
-
-
-
45
-
-
79251488241
-
-
Modeling of the distillation was carried out using Dynochem modeling software.
-
Modeling of the distillation was carried out using Dynochem modeling software.
-
-
-
-
46
-
-
79251486431
-
-
note
-
This was determined by setting the target after distillation to 10 volumes of solvent composed of 4:1 ethanol/water. To reach this endpoint, Dynochem modeling of the azeotropic system showed a starting volume of 36.2 volumes composed of 6.7:1 ethanol/water to be required.
-
-
-
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