Dimethylformamide → HCID 145857610, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2 M i-PrMgCl in THF (1.1 mL, 2.2 mmol) was added dropwise at 0° C. to {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.5 g, 1.0 mmol) (Example 27c) in 5.0 mL THF. The solution was stirred for 20 mins at 0° C., then cooled to −78° C. and a solution of 2.5 M n-BuLi in hexanes (0.6 mL, 1.5 mmol) was added. The mixture was stirred for 5 mins then N,N-dimethylformamide (0.30 mL, 3.8 mmol) was added at −78° C. and the mixture allowed to attain RT. The reaction was quenched with sat. NH4Cl (10 mL) and extracted with EtOAc (3×20 mL), dried over Na2SO4 and evaporated. The crude solid was purified by elution from a 20 g SPE with 50% EtOAc/hex to give 0.33 g (75%) of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1H), 8.48 (s, 1H), 8.26 (m, 1H), 8.10 (m, 1H), 8.06 (s, 1H), 7.71 (s, 1H), 2.50 (s, 3H), 1.51 (s, 9H). Mass spectrum (ESI, m/z) calcd. for C18H20N2O5S3 440.1, found 440.8 (M+H).

Provenance & Evidence