Potassium Hydroxide → HCID 59454997, compound

Participants

Reaction Steps

2-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-cyclopropyl-1-(4-fluorophenyl)ethanol (398 g, 1 mmol) was dissolved thionyl chloride (3 mL) and stirred for 5 min. at RT. The solution was heated at 50° C. for 2 h. Excess thionyl chloride was removed under reduced pressure and the residue was dissolved in N-methyl-2-pyrrolidone (3 mL). KOH (472 mg, 8.4 mmol) was added and the reaction mixture was heated at 100° C. for 2 h. The reaction mixture was cooled to RT and diluted with ice-cold water. The aqueous layer was extracted with EtOAc, the organic layer was washed with water, dried over sodium sulfate, and concentrated, under reduced pressure. The residue was purified by silica gel chromatography (100-200 mesh) eluting with 2% MeOH-DCM followed by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.58 (s, 1H), 7.48 (m, 2H), 7.20 (m, 4H), 6.60 (s, 1H), 6.0 (d, 1H), 5.80 (m, 1H), 4.75 (m, 2H), 4.40 (m, 1H), 3.82 (m, 1H), 3.58 (m, 1H), 3.20 (m, 1H), 3.10 (s, 3H), 2.0 (d, 3H).

Provenance & Evidence