Dimethylformamide → HCID 23393847, compound

Participants

Reaction Steps

2-Methyl-3-benzyloxycarbonyl-5-hydroxyindole (5.90 g, 21.0 mmol, 1 eq) was suspended in dry CH2Cl2 (100 mL) and dry DMF (2 mL) under Ar. Triethylamine (8.77 mL, 63 mmol, 3 eq) was added followed by the addition of perfluorobutanesulfonyl fluoride (4.2 mL, 23.4 mmol, 1.1 eq). The reaction mixture was stirred at room temperature and followed by TLC (CH2Cl2/MeOH 98/2). After 18 hours, the reaction was quenched with aqueous hydrochloric acid. The organic phase was washed with water (2×) and the combined aqueous phases extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed eluting with methanol/CH2Cl2(98/2). 10.17 g (86% yield) of the indole-nonaflate was obtained as a white solid.

Provenance & Evidence