Tetrabutylammonium Fluoride → HCID 58345120, compound

Participants

Reaction Steps

N-(4-(2-(2-aminopyridin-3-yl)-6-(1H-pyrrol-3-yl)-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)benzamide was synthesized according to General Procedure A followed by General Procedures I, B and C and subsequent TBAF-deprotection. TBAF-deprotection: To a solution of N-(4-(2-(2-aminopyridin-3-yl)-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)benzamide (5.2 g) in anhydrous tetrahydrofuran (100 ml) was added 1.0 M tetrabutylammonium fluoride (TBAF) in tetrahydrofuran (3 ml). The reaction was stirred at room temperature for 1 hour. The reaction was diluted with water (300 ml), dichloromethane (200 ml) and methanol (50 ml) and stirred for 1 hour. The organics were separated and the aqueous was washed with dichloromethane (1×200 ml). The organics were combined, washed with water (2×200 ml), brine (1×100 ml), dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (30% ethyl acetate in dichloromethane to 5% methanol/25% ethyl acetate in dichloromethane) gave the product as a yellow solid. Further trituration with ether and hexanes gave a light yellow solid (1.2 g, 41%). 400 M Hz 1H NMR (DMSO-d6) δ: 11.02 (s, 1H), 9.17-9.11 (m, 1H), 8.55 (s, 1H), 8.29 (s, 1H), 8.00-7.96 (m, 1H), 7.93 (d, J=7.6 Hz, 2H), 7.58-7.33 (m, 8H), 7.21 (d, J=7.6 Hz, 1H), 7.04 (s, 2H), 6.85 (s, 1H), 6.56 (s, 1H), 6.40 (t, J=6.0 Hz, 1H), 4.58 (d, J=6.0 Hz, 2H); LCMS: 486 [M+H]. Calc. for C29H23N7O 0.18 water 0.02 ethyl acetate 0.08 dichloromethane: C, 70.42; H, 4.80; N, 19.71. Found C, 70.41; H, 4.78; N, 19.71.

Provenance & Evidence