Dimethyl Sulfate → HCID 22676827, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (192 mg, 0.800 mmol) was added to a cooled (0° C.) and stirred solution of 3-(4-tert-butylphenyl)-5-[(cyclopropylcarbonyl)amino]-1-(3-methoxybenzyl)-1H-indole-2-carboxylic acid (Example 167, 94.5 mg, 0.190 mmol) in tetrahydrofuran (5 mL). The cold bath was removed and stirring was continued for 1 h. Dimethylsulfate (0.75 mL, 101 mg, 0.80 mmol) was added and the reaction was stirred for an additional 2 h. The reaction was quenched with water (50 mL) and then extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Flash chromatography of the residue over silica gel using 40% ethyl acetate/hexane afforded 894 mg (90%) of the desired product. The product had: 1H NMR (300 MHz, CDCl3) δ 7.38-7.50 (m, 3 H), 7.28-7.36 (m, 3 H), 7.11-7.24 (m, 2 H), 6.59-6.76 (m, 3 H), 5.70 (s, 2 H), 3.90 (s, 3 H), 3.69 (s, 3 H) 3.21 (s, 3 H), 1.34 (s, 9 H), 1.15-1.35 (m, 1 H), 0.87-0.97 (m, 2 H), 0.48-0.58 (m, 2 H); mass spectroscopy gave MH+=525.3 (calc'd exact mass for C33H36N2O4=524.27).

Provenance & Evidence