Triphenylphosphine → 5-[3-Methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine

Participants

Reaction Steps

[C1] A solution of di-tert-butyl azodicarboxylate (37.9 mg) in dichloromethane (1 ml) was added to a stirred suspension of 4-(6-amino-5-(oxazolo[5,4-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol (50 mg), triphenylphosphine (43 mg) and 2-(pyrrolidin-1-yl)ethanol (19 mg) dissolved in dichloromethane (4 ml) under nitrogen. The resulting suspension was stirred at room temperature for 1 hour. Triphenylphosphine (43 mg) and a solution of DTAD (37.9 mg) in dichloromethane (1 ml) were added. The resulting mixture was stirred at room temperature for 20 minutes. After evaporation of the solvents, the residue was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane and methanolic ammonia (7 N) in dichloromethane. After collection of the desired fractions and evaporation of the solvents, the resulting solid was triturated with acetonitrile to give 5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine (20 mg) as a solid. NMR Spectrum: (DMSOd6) 1.66-1.73 (m, 4H), 2.51-2.58 (m, 4H), 2.81 (t, 2H), 3.88 (s, 3H), 4.09 (t, 2H), 7.07 (d, 1H), 7.21 (dd, 1H), 7.28 (d, 1H), 7.53 (dd, 1H), 7.78 (bs, 2H), 8.30 (dd, 1H), 8.40 (dd, 1H), 8.47 (d, 1H), 8.60 (d, 1H)

Provenance & Evidence