Lithium iodide → HCID 25142576, compound

Participants

Reaction Conditions

Reaction Steps

(1R,2R)-N-(1-cyanocyclopropyl)-2-[(5-methoxycarbonylmethyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)carbonyl]cyclohexanecarboxamide (150 mg, 0.32 mmol) and lithium iodide (520 mg, 3.89 mmol) were suspended in pyridine (5 mL) in a capped microwave vessel. This was heated in a microwave at 150° C. for one hour (absorbance: N). Pyridine was removed in vacuo and the residue azeotroped once with toluene. It was taken up in 50% brine (20 mL), acidified with acetic acid and partitioned with ethyl acetate (2×80 mL). Combined organics were dried (magnesium sulphate), concentrated in vacuo, azeotroped once with toluene and adsorbed onto silica for purification by flash chromatography (0-20% methanol/DCM). This gave (1R,2R)-N-(1-cyanocyclopropyl)-2-[(5-hydroxycarbonylmethyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)carbonyl]cyclohexanecarboxamide as a pale yellow solid (84.0 mg, 59%).

Provenance & Evidence