Diisopropylethylamine → (1R,3R)-3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol

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Reaction Conditions

Reaction Steps

A stirred suspension of 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (24.5 g, 72.6 mmol) in methanol (120 ml) was treated with (1R,3R)-3-Amino-cyclohexanol* (8.9 g, 76.3 mmol) and N,N-diisopropylethylamine (13.3 mL, 76.3 mmol), and stirred at 65° C. for three hours. The mixture was then cooled and 10% palladium on carbon (7.6 g, 3.6 mmol) was added. The mixture was pressurized to 100 psi with hydrogen and stirred at 50° C. for 18 h. Filtration and concentration afforded the desired product which was carried on directly into the next step. LCMS (Method P, ESI): RT=2.17 min, m+H=387.1. *Prepared following the procedures described in: P. Bernardelli et al./Tetrahedron: Asymmetry 15 (2004) 1451-1455

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