Lithium Hydroxide → 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

Participants

Reaction Steps

A solution of Example 171a (0.100 g, 0.16 mmol) in 9 mL tetrahydrofuran/methanol (2:1) was treated with 1N lithium hydroxide (0.024 g, 1.00 mmol) in 1 mL water at room temperature for 16 hours. The material was diluted with water and resulting precipitate collected by filtration. Trituration with dimethyl sulfoxide/methanol and filtration afforded 54 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 1.11-1.44 (m, 5H) 1.54-1.66 (m, 1H) 1.67-1.80 (m, 2H) 1.87-1.99 (m, 2H) 3.62-3.77 (m, 1H) 6.78 (d, J=7.93 Hz, 1H) 6.86 (d, J=4.36 Hz, 2H) 8.23 (s, 1H) 8.37 (s, 1H) 8.49 (s, 1H) 12.41 (s, 1H). MS (ESI−) m/z 405.1 (M−H)−.

Provenance & Evidence