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34548742868
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Typical Procedure for Acylation: At r.t. and under an inert atmosphere, AlCl3 (714 mg, 5.36 mmol, 4.5 equiv) and acetyl chloride (178 μL, 2.38 mmol, 2 equiv) were added to a suspension of 4a (0.2 M, 200 mg, 1.19 mmol) in anhyd CH2Cl2. The mixture was stirred at reflux until completion of the reaction (monitored by TLC, In the case of methyl oxalyl chloride and oxalyl chloride, the chloride was added as a 50% solution in CH2Cl2 and the reaction was stirred at r.t. The resulting mixture was then cautiously quenched at 0°C with H 2O. The mixture was extracted with a mixture of EtOAc-DMF (99:1, The resulting organic layer was washed with a sat. aq NaHCO3 solution and brine, dried over MgSO4, filtered, and solvents were removed under reduced pressure. Trituration of the crude residue from MeOH followed by filtration afforded 6-acetylpyrido[2,3-b]indole 5a (168 mg) as
-
2O: C, 74.27; H, 4.79; N, 13.32. Found: C, 74.35; H, 4.81; N, 13.26.
-
-
-
-
34
-
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34548744591
-
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Analytical Data of Compound 6: The compound 6 was obtained by flash chromatography [gradient: EtOAc-PE (1:1) → EtOAc, yield: 90, white solid; mp 207°C (MeOH, IR (KBr, 3049, 2850, 1734, 1622, 1599, 1496, 1473, 1408, 1234, 1201,752 cm-1. 1H NMR (300 MHz, DMSO-d6, δ, 12.5 (brs, 1 H, NH, 8.86 (d, J, 1.5 Hz, 1 H, H-5, 8.74 (dd, J, 1.6, 7.8 Hz, 1 H, H-4, 8.52 (dd, J, 1.6, 4.9 Hz, 1 H, H-2, 8.05 (dd, J, 1.5, 8.6 Hz, 1 H, H-7, 7.66 (d, J, 8.6 Hz, 1 H, H-8, 7.33 (dd, J, 4.9, 7.8 Hz, 1 H, H-3, 4.00 (s, 3 H, Me, 13C NMR (75 MHz, DMSO-d6, δ, 186.2 (CO, 165.3 (CO, 152.7 (C, 147.9 (CH, 143.2 (C, 129.7 (CH, 127.9 (CH, 125.1 (CH, 123.4 (C, 120.7 (C, 116.4 (CH, 115.3 (C, 112.0 (C, 52.9 (Me, MS ESI, m/z, 255 [M, H, Anal. Calcd for C14H10N2O3: C, 66.14; H, 3
-
3: C, 66.14; H, 3.96; N, 11.02. Found: C, 66.22; H, 4.03; N, 10.92.
-
-
-
-
35
-
-
34548764923
-
-
Analytical Data of Compound 7: The compound 7 was obtained by trituration from MeOH; yield: 71, white solid; mp >295°C (MeOH, IR (KBr, 3219, 1682, 1597, 1493, 1476, 1405, 909, 746 cm-1. 1H NMR (300 MHz, DMSO-d6, δ, 12.73 (br s, 1 H, OH, 12.18 (br s, 1 H, NH, 8.83 (br s, 1 H, H-5, 8.66(dd, J, 1.6, 7.6 Hz, 1 H, H-4, 8.47 (dd, J, 1.6, 4.9 Hz, 1 H, H-2, 8.06 (dd, J, 1.7, 8.6 Hz, 1 H, H-7, 7.55 (d, J, 8.6 Hz, 1 H, H-8, 7.27 (dd, J, 4.9, 7.6 Hz, 1 H, H-3, 13C NMR (75 MHz, DMSO-d6, δ, 167.9 (CO, 152.5 (C, 146.8 (CH, 141.7 (C, 129.2 (CH, 127.9 (CH, 123.5 (CH, 121.9 (C, 120.2 (C, 115.8 (CH, 115.4 (C, 111.0 (CH, MS (EI, m/z, 212 [M+·, HRMS EI, m/z calcd for C12H8N2O2: 212.0586; found: 212.0584
-
2: 212.0586; found: 212.0584.
-
-
-
-
36
-
-
34548748095
-
-
Analytical Data for Compound 8: The compound 8 was obtained by flash chromatography [gradient: EtOAc-PE (1:1) → EtOAc, yield: 78, white solid; mp 212°C (MeOH, IR (KBr, 3040, 1647, 1603, 1565, 1494, 1466, 1254, 769, 702 cm-1. 1H NMR (300 MHz, DMSO-d 6, δ, 12.29 (br s, 1 H, NH, 8.65-8.67 (m, 2 H, H-4, H-5, 8.48 (dd, J, 1.5, 4.9 Hz, 1 H, H-2, 7.90 (dd, J, 1.5, 8.0 Hz, 1 H, H-7, 7.76-7.79 (m, 2 H, Har, 7.56-7.68 (m, 4 H, H-8, H ar, 7.26 (dd, J, 4.9, 8.0 Hz, 1 H, H-3, 13C NMR (75 MHz, DMSO-d6, δ, 195.5 (CO, 152.6(C, 147.0 (CH, 141.7 (C, 138.3 (C, 132.0 (CH, 129.5 (2 x CH, 129.4 (CH, 128.7 (CH, 128.6 (C, 128.5 (2 x CH, 124.3 (CH, 120.4 (C, 115.9 (CH, 115.5 (C, 111.1 (CH, MS ESI, m/z, 273 [M, H, Anal. Calcd for C 18H12N2O: C, 79.40; H, 4.44; N, 10.29. Found
-
2O: C, 79.40; H, 4.44; N, 10.29. Found: C, 79.48; H, 4.44; N, 10.29.
-
-
-
-
37
-
-
0036395623
-
-
(a) Mayer, S.; Joseph, B.; Gurllaumet, G.; Merour, J.-Y. Synthesis 2002, 1871.
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(2002)
Synthesis
, pp. 1871
-
-
Mayer, S.1
Joseph, B.2
Gurllaumet, G.3
Merour, J.-Y.4
-
38
-
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27744459758
-
-
(b) Lee, T. H.; Tong, K. L.; So, S. K.; Leung, L. M. Synth. Met. 2005, 155, 116.
-
(2005)
Synth. Met
, vol.155
, pp. 116
-
-
Lee, T.H.1
Tong, K.L.2
So, S.K.3
Leung, L.M.4
-
40
-
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34548794792
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-
Typical Procedure and Analytical Data for Compound 9: At -78°C and under an inert atmosphere, AlCl3 (714 mg, 5.36 mmol, 4.5 equiv) was added portionwise to a suspension of 4a (0.02 M, 200 mg, 1.19 mmol) in anhyd CH2Cl2. After stirring for 5 min, α,α-dichloromethyl methyl ether (318 μL, 3.57 mmol, 3 equiv) was added dropwise to the mixture. The reaction mixture was stirred at -78°C and then allowed to warm to r.t. for 12 h. The resulting mixture was then cautiously quenched at 0°C with H2O and extracted with a mixture of EtOAc-DMF (99:1, The combined organic layers were washed with a sat. aq NaHCO3 solution, dried with MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc-PE, 1:1) to afford 9 (100 mg, 46, as a white solid; mp 262°C (MeOH, IR KBr, 3043, 3014, 2824, 1690, 1604, 1569, 1470, 1410, 761 cm
-
2O: C, 73.46; H, 4.11; N, 14.28. Found: C, 73.15; H, 4.39; N, 14.28.
-
-
-
-
41
-
-
34548768212
-
-
Typical Procedure and Analytical Data for Compound 10: At r.t. and under an inert atmosphere, a solution of bromine (1.2 equiv, 0.7 M) in anhyd CH2Cl2 was added to a suspension of 4a (0.45 M, 200 mg, 1.19 mmol) in anhyd CH2Cl2. The mixture was stirred for 1 h at r.t. Excess bromine was destroyed by addition of a sat. aq Na 2S2O3 solution. The resulting mixture was extracted with EtOAc-DMF (99:1, The combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. Trituration of the crude residue from MeOH followed by filtration afforded 10 (241 mg, The filtrate was evaporated and purified by flash chromatography [gradient: EtOAc-PE (1:1) → EtOAc] to give additional 10 (27 mg, yield: 91, mp 250°C (MeOH, lit.15a mp 266-270°C, IR KBr, 3052, 1604, 1586, 1493, 1448, 768, 610 cm -1
-
2: 245.9793; found: 245.9797
-
-
-
-
43
-
-
27744604033
-
-
Yang, X.; Xi, C.; Jiang, Y. Tetrahedron Lett. 2005, 46, 8781.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 8781
-
-
Yang, X.1
Xi, C.2
Jiang, Y.3
-
44
-
-
34548750353
-
-
2 salt suggests a possible involvement of an N-nitro intermediate. Further studies are underway to clarify the origin of the selectivity.
-
2 salt suggests a possible involvement of an N-nitro intermediate. Further studies are underway to clarify the origin of the selectivity.
-
-
-
-
45
-
-
34548794793
-
-
Analytical Data for Compound 13: mp >295°C (MeOH, lit.15a mp >320°C, IR (KBr, 3066, 1612, 1587, 1573, 1498, 1456, 1327, 749 cm-1. 1H NMR (300 MHz, DMSO-d 6, δ, 12.58 (brs, 1 H, NH, 9.25 (d, J =2.2 Hz, 1 H, H-5, 8.80 (dd, J, 1.7, 7.8 Hz, 1 H, H-4, 8.54 (dd, J, 1.7, 4.8 Hz, 1 H, H-2, 8.35 (dd, J =2.2, 9.0 Hz, 1 H, H-7, 7.65 (d, J, 9.0 Hz, 1 H, H-8, 7.35 (dd, J, 4.8, 7.8 Hz, 1 H, H-3, 13C NMR (75 MHz, DMSO-d6, δ, 153.0 (C, 147.9 (CH, 142.6 (C, 140.5 (C, 130.2 (CH, 122.2 (CH, 120.3 (C, 118.4 (CH, 116.6 (CH, 115.5 (C, 111.6 (CH, MS (ESI, m/z, 214 [M, H, HRMS ESI, m/z [M, H, calcd for C11H7N 3O2: 214.0617; found: 214.1017
-
2: 214.0617; found: 214.1017.
-
-
-
-
46
-
-
34548713457
-
-
Analytical Data for Compound 14: mp 253°C (MeOH, IR (KBr, 3046, 1600, 1573, 1525, 1474, 1362, 732 cm-1. 1H NMR (300 MHz, DMSO-d6, δ, 12.15 (br s, 1 H, NH, 8.63 (dd, J, 1.5, 7.7 Hz, 1 H, H-4, 8.62 (d, J, 7.7 Hz, 1 H, H-7, 8.58 (dd, J, 1.5, 4.8 Hz, 1 H, H-2, 8.35 (d, J, 8.2 Hz, 1 H, H-5, 7.43 (dd, J, 7.7, 8.2 Hz, 1 H, H-6, 7.36 (dd, J, 4.8, 7.7 Hz, 1 H, H-3, 13C NMR (75 MHz, DMSO-d6, δ, 152.4 (C, 147.6 (CH, 132.1 (C, 131.9 (C, 128.9 (CH, 128.1 (CH, 124.5 (C, 122.1 (CH, 118.9 (CH, 116.5 (CH, 114.0 (CH, MS (EI, m/z, 213 [M+·, HRMS EI, m/z calcd for C11H 7N3O2: 213.0538; found: 213.0535
-
2: 213.0538; found: 213.0535.
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-
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