Dimethylformamide → (4-{3-[(2,3-difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclohex-3-enyl)-carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

To a solution of the above boronic ester (1.0 g, 2.5 mmol), trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester (690 mg, 2.0 mmol, prepared from (4-Oxo-cyclohexyl)-carbamic acid tert-butyl ester (Heterocycles 58 (2002) 471-504)) in a mixed solvent of DMF (15 ml) and DMSO (6 ml) was added aqueous 2.0M Na2CO3 (2 ml, 4 mmol) and PdCl2(PPh3) 2 The mixture was degassed and heated at 80° C. under Argon for 72 h, and then concentrated under high vacuum to remove DMF. The residue was suspended in aqueous NaHCO3, then filtered. The solid was purified for FC to give (4-{3-[(2,3-difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclohex-3-enyl)-carbamic acid tert-butyl ester as a white solid (530 mg) in 56% yield, LC-MS: m/e=468.4 (M+H), 466.4 (M−H). 1H-NMR (500 MHz, CDCl3) 13.41 (br.s, 1H), 9.23 (s, 1H), 8.44 (s, 1H), 8.38 (s, 1H), 7.09 (m, 3H), 6.24 (s, 1H), 4.56 (br. s, 1H), 4.32 (s, 2H), 3.90 (br.s, 1H), 2.63 (m, 3H), 2.13 (m, 2H), 1.28 (m, 1H), 1.49 (s, 9H).

Provenance & Evidence