Diisopropylethylamine → HCID 178526773, compound

Participants

Reaction Steps

1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (50.0 g, 148 mmol) was suspended in isopropanol (400 mL) and DIPEA (35.0 mL, 207 mmol) was added, followed by trans-4-aminocyclohexanol (18.7 g, 163 mmol). The mixture was heated at reflux for 2 hours, then cooled and concentrated under vacuum. The residue was dissolved in dichloromethane and washed with water (added 1 N HCl to bring pH to 6-7). The organic layer was dried (Na2SO4) and concentrated under vacuum. The residual foam was taken up in ethanol and the resulting precipitate collected to give 65.0 g (quant) of crude trans 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol. NMR (400 MHz, CDCl3) δ: 9.10 (s, 1H), 9.03 (d, 1H), 8.19 (dd, 2H), 7.62 (m, 2H), 7.52 (m, 2H), 6.71 (d, 1H), 3.95 (m, 1H), 3.79 (m, 1H), 3.78-3.67 (m, 2H), 2.22 (m, 2H), 2.08 (m, 2H), 1.59 (m, 1H), 1.54 (m, 4H).

Provenance & Evidence