4-Iodoaniline → HCID 59426272, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-cyclobutyl-6-morpholin-4-yl-1H-indole-3-carbonitrile (1.20 g, 4.27 mmol), triisopropylborate (1.28 mL, 5.55 mmol) in THF (15 mL) at −78° C. was added LDA (1.5M mono THF in cyclohexane, 3.27 mL, 4.91 mmol) with stirring. The mixture was stirred at −78° C. for 10 minutes and at room temperature for 30 min followed by the addition of 4-iodoaniline (1.03 g, 4.70 mmol) and PdCl2 (dppf) (0.16 g, 0.2 mmol). The reaction system was cooled to −78° C., flushed with nitrogen followed by the addition of DMF (30 mL) and aq. K2CO3 (2.0M, 6.4 mL, 12.8 mmol). The cooling bath was removed and the mixture was stirred overnight and poured into ice water (500 mL). The precipitate was filtered, washed with water, dried in air and purified on silica gel (CH2Cl2/EtOAc, 9:1) to give 2-(4-amino-phenyl)-1-cyclobutyl-6-morpholin-4-yl-1H-indole-3-carbonitrile (1.49 g, 94%).

Provenance & Evidence