Diisopropylethylamine → HCID 67342783, compound

Participants

Reaction Steps

To a solution of 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (580 mg, 1.7 mmol) in n-butanol (20 mL) were added diisopropylethylamine (DIPEA) (1.4 mL, 8.4 mmol) and 3-Amino-3-methyl-piperidine-1-carboxylic acid benzyl ester (420 mg, 1.7 mmol). The mixture was heated to reflux overnight, and LCMS showed 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine consumed. The reaction mixture was purified by column chromatography (eluting with 30˜35% ethyl acetate in hexane) to give 400 mg (43%) of 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-3-methyl-piperidine-1-carboxylic acid benzyl ester. LCMS (Method J, ESI): RT=1.32 min, m+H=549.8; 1H NMR (400 MHz, CDCl3) δ: 9.60 (s, 1H), 9.10 (s, 1H), 8.20 (m, 2H), 7.70-7.50 (m, 4H), 7.40-7.30 (m, 5H), 5.34 (m, 2H), 3.90-3.80 (m, 1H), 2.30-2.20 (m, 1H), 1.90-1.50 (m, 9H).

Provenance & Evidence