Hexamethyldisilazane → HCID 10021156, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-1,4-dihydroindeno[1,2-c]pyrazole (250 mg, 0.6 mmol), hexamethyldisilazane (0.9 ml, 4.2 mmol), diisopropylethylamine (0.2 ml, 1.2 mmol) and 1,3-bis(diphenylphosphino)propane (25 mg, 0.06 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (5 ml) was degassed with nitrogen for 0.5 h, Pd(OAc)2 (13 mg, 0.06 mmol) was added and carbon monoxide was bubbled through the reaction whilst heating to 100° C. After 2 h the stream of carbon monoxide was replaced with a balloon of carbon monoxide and the reaction was heated at 100° C. for 16 h. The reaction was cooled, partitioned between H2O and EtOAc and the organic layer washed with H2O (×10), dried (MgSO4) and evaporated. The residue was chromatographed on silica, eluting with 3% methanol/dichloromethane to give a yellow oil which was crystallised from CDCl3 to give the title compound as a white solid (40 mg, 19%). 1H NMR (360 MHz, CDCl3) δ 7.92 (s, 1H), 7.81 (s, 1H), 7.51 (d, J=6.8 Hz, 2H), 7.47–7.37 (m, 3H), 3.33 (s, 2H), 2.60 (s, 3H), m/z (ES+) 357 (M+H)+.

Provenance & Evidence