tert-Butyl 4-sulfanylpiperidine-1-carboxylate → HCID 58266610, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed suspension of 5-bromo-3-(1-methyl-1H-pyrazol-4-yl)-9-(2-trimethylsilanylethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (120 mg, 0.25 mmol), 4-mercaptopiperidine-1-carboxylic acid tert-butyl ester (54 mg, 0.25 mmol) and sodium tert-butoxide (26.4 mg, 0.28 mmol) in dimethoxyethane (0.4 mL) in a sealed 5 ml microwave vial was added a degassed solution of palladium(II) acetate (2.2 mg, 0.01 mmol) and (R)-(−)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (5.5 mg, 0.01 mmol) in dimethoxyethane (1.0 mL). The reaction mixture was heated at 100° C. for 22 h then cooled to ambient temperature and concentrated in vacuo. The resultant residue was adsorbed onto HM-N then purified by flash chromatography (silica, 50 g column, Si-SPE, 0-10% (2M ammonia in MeOH) in DCM) to afford the title compound as a yellow solid (106 mg, 68%). 1H NMR (DMSO-D6, 300 MHz): 9.33 (s, 1H), 9.11-9.06 (m, 2H), 8.35 (s, 1H), 8.05-8.01 (m, 1H), 6.05 (s, 2H), 3.93 (s, 3H), 3.86-3.73 (m, 2H), 3.64-3.53 (m, 2H), 2.97-2.78 (m, 3H), 1.97-1.83 (m, 2H), 1.64-1.45 (m, 2H), 1.35 (s, 9H), 0.87-0.78 (m, 2H), −0.17 (s, 9H).

Provenance & Evidence