5-Aminoindole → 4-[7-Benzenesulfonyl-4-(1H-indol-5-ylamino)-7H-pyrrolo[2,3-d]-pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

4-(7-Benzenesulfonyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (150 mg, 0.31 mmol) in butanol (5 mL) was treated with 5-aminoindole (50 mg, 0.38 mmol) and heated to 80° C. for 2 h and then 85° C. for 1 h. The mixture was evaporated to dryness and pre-absorbed onto silica. Purification on silica by elution with dichloromethane:methanol (97:3) yielded a slightly pink solid. 1H NMR (d6-DMSO, 400 MHz) 9.4(NH), 8.3(1H, s), 8.0(2H,d), 7.9(1H,s), 7.7(1H,m), 7.6(2H,m), 7.4(2H,m), 7.2(1H,m), 6.8(1H, br.s), 6.4(1H, s), 6.0(1H,s), 4.1(2H, m), 3.6(2H,m), 2.5(2H, m), and 1.5(9H, s); LC/MS: m/z 570 [M+H]+, Rt=4.07 min.

Provenance & Evidence