Triethylamine → HCID 178435487, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of (R)-indan-1-yl-(6-vinyl-4H-benzo[d][1,3]oxazin-2-yl)-amine (Example 134) (250 mg, 0.86 mmol), 3-bromopyridine (177 mg, 1.12 mmol), tri(o-tolyl)phosphine (21 mg, 0.07 mmol), triethylamine (261 mg, 2.58 mmol) and palladium actetate (7.73 mg, 0.034 mmol) in N,N-dimethylformamide (3 ml) was heated in a sealed tube at 100° C. for 3 h. The reaction mixture was poured into water (20 ml), extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with water (2×20 ml) and brine (20 ml), dried (magnesium sulfate) and evaporated. Further purification by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/heptane) yielded the title compound as yellow solid (70 mg, 22%). MS (ISP): m/e=368.2 (M+H+); m.p. 132° C.

Provenance & Evidence