Ethyl Acetate → HCID 53354589, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of N-(1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(2-hydroxypropan-2-yl)benzamide (Example 9, 75 mg, 0.215 mmol) in DCM (4 ml) was added NBS (38.2 mg, 0.215 mmol). The reaction mixture was stirred at 50° C. for 1 h, and then subjected to chromatography (NH—SiO2, EtOAc). The fractions were concentrated in vacuo and purified by preparatory HPLC to give the title compound N-(3-bromo-1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(2-hydroxypropan-2-yl)benzamide (60 mg, 0.14 mmol, 65% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.40-0.48 (m, 2 H) 0.52-0.59 (m, 2 H) 1.20-1.32 (m, 1 H) 1.46 (s, 6 H) 4.05 (d, J=7.07 Hz, 2 H) 5.17 (s, 1 H) 7.59 (d, J=8.59 Hz, 2 H) 7.74 (s, 1 H) 8.02 (d, J=8.59 Hz, 2 H) 8.40 (s, 1 H) 8.51 (s, 1 H) 10.69 (s, 1 H); m.p. 193-194° C.

Provenance & Evidence