Methanol → HCID 22058242, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-1,4-dihydroindeno[1,2-c]pyrazole (1 g, 2.6 mmol), triethylamine (0.7 ml, 5.2 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (178 mg, 0.32 mmol) in methanol (5 ml) and N,N-dimethylformamide (10 ml) in a sealed tube filled with carbon monoxide was added Pd(OAc)2 (36 mg, 0.16 mmol) and the mixture heated to 100° C. for 16 h. The solvent was evaporated, the residue dissolved in ethanol and treated with sodium hydroxide (13 mmol) at 0° C. and allowed to warm to RT. The solvent was evaporated, the residue partitioned between H2O and EtOAc and the product extracted into the aqueous layer which was then washed with diethyl ether (×3). The aqueous was cooled, acidified and extracted into EtOAc, the organic layer was then extracted with ammonium hydroxide solution (×2) and the aqueous cooled to 0° C. and acidified with conc HCl, left to stand at 0° C until the title compound appeared as a precipitate. 1H NMR (360 MHz, CDCl3) δ 8.08 (t, J=7.8 Hz, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.51 (d, J=7.6 Hz, 1H), 7.45–7.35 (m, 3H), 7.30–7.13 (m, 4H), 3.16 (s, 2H), 2.59 (s, 3H), m/z (ES+) 358 (M+H)+.

Provenance & Evidence