Methyl iodide → HCID 59811527, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromo-7-(2,4-dichloro-phenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (1-2; 0.100 g, 0.277 mmol) in 2 mL of dry THF was cooled to −78° C. in a dry ice-acetone bath under an argon atmosphere and treated with 0.21 mL of 1.6 M n-butyllithium in hexane. After 10 m the mixture was treated with iodomethane (0.21 mL, 0.047 g, 0.33 mmol) and stirred at −78° C. for 1 h and allowed to come to room temperature overnight. The reaction mixture was quenched with 40 mL of saturated ammonium chloride and extracted twice with 25 mL portions of ethyl acetate. The combined the extracts were washed with brine, dried over magnesium sulfate, and evaporated to dryness to yield 79 mg of crude product. Purification by preparative TLC using ethyl acetate/toluene (1:9) afforded 19 mg of 7-(2,4-dichloro-phenyl)-2,3-dimethyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (2-17; 23% theory) as a pink solid: mp 66.6-76.6° C.

Provenance & Evidence