Ammonium Hydroxide → HCID 58495624, compound

Participants

Reaction Steps

Set up reaction in 3 separate flasks. To flask number 1 slurry 2-chloro-5-cyclopentylthiomethyl-pyridine (1 g, 4.4 mmol) and copper(I) cyanide (0.78 g, 8.7 mmol) in DMF (5 mL). To flask number 2 slurry 2-chloro-5-cyclopentylthiolmethyl-pyridine (1 g, 4.4 mmol) and copper(I) cyanide (0.78 g, 8.7 mmol) in DMF (5 mL). To flask number 3 slurry 2-chloro-5-cyclopentyl-thiomethyl-pyridine (2 g, 8.8 mmol) and copper(I) cyanide (1.6 g, 17.6 mmol) in DMF (10 mL). Stir each reaction in a sealed flask at 170° C. for 16 h. Follow the reactions by GC/MS. Cool all reaction flasks to room temperature. Combine the flask contents and pour into a solution of NH4OH (120 mL) and hexane/EtOAc (1:1, 100 mL). Collect the organic phase and extract the aqueous phase twice with hexane/EtOAc (1:1, 100 mL). Concentrate in vacuo the combined organic extracts. Purify by chromatography on silica gel (90 g) eluting with hexane/EtOAc (49:1 to 4:1 gradient) to obtain the desired intermediate (2 g, 40%) that contains approximately 10% starting material. Use the material in the next step without additional purification. MS (APCI+) m/z: 218 (M)+.

Provenance & Evidence