Potassium Carbonate → HCID 67182945, compound

Participants

Reaction Conditions

Reaction Steps

6-Iodo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (7.70 g, 25 mmol), tris(dibenzylideneacetone)dipalladium(0) (482 mg, 0.52 mmol), zinc (202 mg, 3.0 mmol), Zn(CN)2 (1.819 g, 15 mmol), and 1,1′-(diphenylphosphino)ferrocene (572 mg, 1.03 mmol) were dissolved in N,N-dimethylacetamide (40 mL). The reaction was heated at 120° C. for 1 h then cooled to room temperature. The reaction mixture was diluted with CH2Cl2, filtered through diatomaceous earth, and concentrated. The crude material was dissolved in THF (15 mL) and water (3 mL) and treated with K2CO3 (3.74 g, 27 mmol) and (Boc)2O (5.91 g, 27 mmol). After 2 h, the reaction was diluted with water and extracted with CH2Cl2 (4×20 mL). The combined CH2Cl2 layers were dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash column chromatography (silica gel, 5–25% EtOAc/hexanes) to afford 6-cyano-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (5.24 g, 91%) as an oil.

Provenance & Evidence