Water → HCID 22603403, compound

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (114 mg), R-BINAP (69 mg), potassium t-butoxide (294 mg), and morpholine (0.209 ml) were added to a solution of t-butyl 3-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylate (1 g) in de-gassed toluene (6 ml), under an atmosphere of argon. The reaction was stirred and heated at 90° C. for 16 hours then poured into water (50 ml), extracted with ethyl acetate (3×50 ml), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using 10% ethyl acetate:iso-hexane as eluent, to afford the product as a yellow oil (325 mg, 33%); NMR d (CD3SOCD3) 3.20 (t, 4H), 3.73 (t, 4H), 5.56 (s, 2H), 6.88 (d, 1H), 7.7 (t, 1H), 7.25 (m, 2H), 7.50 (m, 2H), 7.80 (d, 1H), M/z (+) 461 (MH+), 405.

Provenance & Evidence