Ethanol → HCID 145857611, compound

Participants

Reaction Steps

The procedure used in Example 1: step c was followed using {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (Example 27 (100 mg, 0.2 mmol)), Pd(PPh3)4 (59 mg, 0.05 mmol), 3-hydroxymethyl-2-methyl-phenylboronic acid ((Example 7: step a) 105 mg, 0.63 mmol), Na2CO3 (2M, 0.8 mL, 1.6 mmol), ethanol (0.8 mL) and toluene (1.6 mL). Analogous aqueous workup and purification of the crude material by SiO2 flash chromatography (25–50% EtOAc in hexanes) yielded the title compound (72 mg, 67%) as a light-yellow glass. 1H-NMR (CDCl3): δ 8.00 (s, 1H), 7.96 (dt, 1H, J=2.1, 4.4 Hz), 7.93 (m, 1H), 7.54 (m, 2H), 7.27 (m, 2H), 7.18 (d, 1H, J=1.4 Hz), 4.68 (s, 2H), 2.54 (s, 3H), 2.20 (s, 3H), 1.51 (s, 9H).

Provenance & Evidence