Sodium Sulfite → HCID 58504870, compound

Participants

Reaction Steps

To 0.29 g (0.77 mmol) of lithum 1-(tert-butoxycarbonyl)-1H-indole-4-sulfinic acid stirring in 1 mL of THF is added 62 mg (0.47 mmol) of NCS. After stirring for 5 minutes, 0.10 g (0.31 mmol) of 3-[3-amino-4-(4-methylpiperidin-1-yl)-4-oxobutyl]benzonitrile is added and the mixture is stirred for 4 h when 10% Na2SO3 and CH2Cl2 are added. The organic phase is dried over Na2SO4, filtered, and concentrated. Preparative TLC (33% EtOAc in hexanes) provides 70 mg (40%) of the sulfonamide. This material (30 mg, 0.053 mmol) in 1 mL of CH2Cl2 is treated with 0.2 mL of TFA for 90 minutes. The mixture is concentrated and purified by preparative TLC (5% MeOH in CH2Cl2) to provide 21 mg (85%) of Example 71. ESI MS Calc. 464.2; Found: 465.7 (M+H)+.

Provenance & Evidence