Methyl 5-bromothiophene-2-carboxylate → HCID 20779309, compound

Participants

Reaction Steps

To a stirred solution of 2-[(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-(4-tributylstannanyl-benzyl)-amino]-3-phenyl-propionic acid methyl ester (100 mg. 0.13 mmol.) in toluene (3 ml.) were added P(Ph3)4Pd (6 mg. 0.039eq.), CuBr (2 mg.) and 5-Bromo-thiophene-2-carboxylic acid methyl ester (26.5 mg, 0.12 mmol.) under nitrogen. The reaction mixture was stirred and heated to reflux during 5 hrs. The progress of the reaction was monitored by TLC. Filtration and removal of the solvent under reduced pressure on a rotary evaporator followed by silica plate for purification using 80% hexane 20% EtOAc afforded 5-(4-{[(1-Methoxycarbonyl-2-phenyl-ethyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-methyl}-phenyl)-thiophene-2-carboxylic acid methyl ester in 41% yield: 1HNMR (Varian 400 MHz, CDCl3) δ8.67(d, 1H, HPh), 8.35 (d, 2H, thiopheneH), 8.10(m, 6H, HPh), 8.00(d, 2H, thiopheneH), 7.38(s, 1H, MTRH), 5.72(m, 3H, NCH2Ph, CHCH2), 4.82(s, 3H, OCH3), 4.68(s, 3H, COOCH3), 4.29(s, 3H, COOCH3), 4.10 (m, 1H, CHCH2), 3.85 (m, 1H, CHCH2), 3.57(s, 3H, ArCH3), 3.40(s, 3H, ArCH3), 3.0(s, 3H, ArCH3) ppm. MS 622.6 (M+).

Provenance & Evidence