1-Methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile → (7-(tert-butylcarbamoyl)-2-(6-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, (2-bromo-7-(tert-butylcarbamoyl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (140 mg, 0.34 mmol) and 1-methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile (crude, containing some 2-methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile) was dissolved in DMF (5 mL) under nitrogen. Pd(PPh3)4 (20 mg, 0.017 mmol) and CuI (13 mg, 0.068 mmol) were added and mixture sonicated for 5 min while bubbling nitrogen. The reaction mixture was stirred at 80° C. for 16 hours. After solvent removal, the residue was purified by column chromatography on silica gel eluting with petroleum ether/EtOAc (3:1 to 1:1, v/v) to give (7-(tert-butylcarbamoyl)-2-(6-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (80 mg, 48.5%). MS: (M+H)+=488.3; 1H NMR (300 MHz, DMSO): δ 9.15 (s, 1H), 8.58-8.53 (m, 3H), 7.83 (s, 1H), 6.31 (s, 2H), 4.25 (s, 3H), 1.52 (s, 9H), 1.10 (s, 9H).

Provenance & Evidence