Early amidation approach to 3-[(4-amido)pyrrol-2-yl]-2-indolinones

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6447-6450

  Manley, Jerad M ^a   Kalman, Monica J ^a   Conway, Brian G ^a   Ball, Cynthia C ^a   Havens, Jeffrey L ^a   Vaidyanathan, Rajappa ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REAGENTS;

SYNTHESIS (CHEMICAL); ZINC;

ORGANIC COMPOUNDS;

3 [(4 AMIDO)PYRROL 2 YL] 2 INDOLINONE; AMIDE; INDOLE DERIVATIVE; N [2 (DIETHYLAMINO)ETHYL] 5 [(5 FLUORO 2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE)METHYL] 2,4 DIMETHYL 1H PYRROLE 3 CARBOXAMIDE; OXIME; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYST; DECARBOXYLATION; DRUG SYNTHESIS; HYDROGENATION;

AMIDES; INDICATORS AND REAGENTS; INDOLES; PYRROLES; ZINC;

EID: 0041573428     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034304q     Document Type: Article

References (13)

1. (a) Tang, P. C.; Miller, T.; Li, X.; Sun, L.; Wei, C. C.; Shirazian, S.; Liang, C.; Vojkovsky, T.; Nematalla, A. S. WO 01/60814.
2. (b) Mendel, D. B.; Laird, A. D.; Xin, X.; Louie, S. G.; Christensen, J. G.; Li, G.; Schreck, R. E.; Abrams, T. J.; Ngai, T. J.; Lee, L. B.; Murray, L. J.; Carver, J.; Chan, E.; Moss, K. G.; Haznedar, J. O.; Sukbuntherng, J.; Blake, R. A.; Sun, L.; Tang, C.; Miller, T.; Shirazian, S.; McMahon, G.; Cherrington, J. M. Clin. Cancer Res. 2003, 9, 327.
3. (a) Fischer, H. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p 202.
4. (b) Treibs, A.; Hintermeier, K. Chem. Ber. 1954, 86, 1167.
5. de Groot, J. A.; Roy, G. M. G-L.; van Koveringe, J. A.; Lugtenburg, J. Org. Prep. Proced. Int. 1981, 13, 97.
6. Beholz, L. G.; Benovsky, P.; Ward, D. L.; Barta, N. S.; Stille, J. R. J. Org. Chem. 1997, 62, 1033.
7. (a) Itoh, K.; Sugihara, H.; Miyake, A.; Tada, N.; Oka, Y. Chem. Pharm. Bull. 1978, 26, 504.
8. (b) Doyle, T. W.; Belleau, B.; Luh, B.-Y.; Conway, T. T.; Menard, M.; Douglas, J. L.; Chu, D. T.-W.; Lim, G.; Morris, L. R.; Rivest, P.; Casey, M. Can. J. Chem. 1977, 55, 484.
9. (a) Winans, C. F.; Adkins, H. J. Am. Chem. Soc. 1933, 55, 4167.
10. (b) Ochiai, E.; Tsuda, K.; Ikuma, S. Chem. Ber. 1935, 68, 1710.
11. Moon, M. W.; Church, A. R.; Steinhards, A. Ger. Offen. DE 2235811, 1973.
12. Battersby, A. R.; Dutton, J. C.; Fookes, C. J. R. J. Chem Soc., Perkin Trans. 1 1988, 1569.
13. Hafner, K.; Bernhard, C. Angew. Chem. 1957, 69, 533.