Water → methyl 2-(1-benzyl-3-bromo-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate

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Reaction Steps

A solution of methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate (480 mg, 0.974 mmol) in N,N-Dimethylformamide (DMF) (1 mL) was treated with NBS (173 mg, 0.974 mmol) and then stirred at room temperature for 20 minutes. Water was added and then mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-50% ethyl acetate/hexanes) to afford methyl 2-(1-benzyl-3-bromo-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate (450 mg, 0.787 mmol, 81% yield) as a pale yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.45-7.28 (m, 9H), 7.03-7.01 (m, 1H), 5.91-5.76 (m, 2H), 5.09 (s, 1H), 3.77 (s, 3H), 3.65 (s, 3H), 1.00 (s, 9H); LCMS (m/z) ES+=571 (M+1).

Provenance & Evidence