Dichloromethane → HCID 66799807, compound

Participants

Reaction Steps

A mixture of 3-{[(4-bromo-5-chlorothiophen-2-yl)sulfonyl]amino}-2-hydroxybenzoic acid (Intermediate 22) (20.6 mg, 0.050 mmol), 2,5-difluorophenylboronic acid (8.7 mg, 0.055 mmol), DIPEA (35 μL, 0.200 mmol) and Pd(dppf)Cl2.CH2Cl2 (2 mg, 0.003 mmol) in aqueous dioxane (1 mL, 9:1 dioxane/water) was heated at 80° C. under nitrogen atmosphere over night. The reaction mixture was acidified by addition of TFA (50 μL). After being allowed to settle overnight the reaction mixture was filtered, diluted with MeOH and purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes) to give 9.7 mg of the title compound (44%). 1H NMR (500 MHz, MeOH-d4) δ ppm 6.90 (t, J=7.94 Hz, 1 H) 7.14 (dddd, J=8.67, 5.60, 2.93, 0.46 Hz, 1 H) 7.16-7.21 (m, 1 H) 7.20-7.25 (tdd, J=8.96, 4.60, 0.46 Hz, 1 H) 7.34 (d, J=1.59 Hz, 1 H) 7.65 (dd, J=7.94, 1.65 Hz, 1 H) 7.74 (dd, J=7.94, 1.65 Hz, 1 H); MS (ESI+) m/z 446 [M+H]+.

Provenance & Evidence