Water → HCID 57844172, compound

Participants

Reaction Steps

1 g (1H-indole-6-yl)-methanol (1.0 g, 6.79 mmol) in DCM (25 mL) was added DBU (1.24 g, 8.15 mmol) and tert-butyldimethylsilylchloride (1.14 g, 7.54 mmol). The reaction mixture was stirred 16 hours before water (25 mL) was added. The phases were separated and the organic phase was washed with HCl (0.1 N, 25 mL) and sodium bicarbonate (sat., 25 mL) and dried MgSO4. The solvent was removed in vacuo to give 1.6 g (90%) 6-(tert-butyldimethylsilanyloxymethyl)-indole. This was converted to 1-cyclopropylmethyl-6-hydroxymethyl-1H-indole-3-carboxylic acid thiazol-2-ylamide using general procedure A where R5X=cyclopropyl-methylbromide; NH2A=2-aminothiazole.

Provenance & Evidence