t-Butylammonium fluoride → 3-(2-Fluoro-4-iodo-phenylamino)-1-(2-hydroxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-hydroxy-ethoxy)-amide

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Reaction Steps

To a solution of 3-(2-fluoro-4-iodo-phenylamino)-1-(2-triisopropylsilanyloxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide (58 mg, 0.085 mmol) in THF (2 mL) was added a 1M solution of tert-butylammonium fluoride in THF (0.1 mL, 0.1 mmol). The reaction mixture was stirred at room temperature for 1 hour and passed through a 5 g SCX-2 cartridge eluting with MeOH then 2M solution of ammonia in MeOH. The appropriate fractions were combined and concentrated to give a residue that was purified by flash chromatography (Si-PPC, MeOH:DCM, gradient 0:100 to 30:70). The title compound was obtained as a yellow solid (16 mg, 38%). LCMS (method A): RT=5.13 min, M+H+=501. 1H NMR (CDOD) 3.70 (2H, m), 3.90 (2H, t, J=5.3 Hz), 3.94 (2H, m), 4.60 (2H, t, J=5.3 Hz), 6.42 (1H, t, J=8.9 Hz), 7.2 (1H, m), 7.43 (1H, dd, J=10.9, 1.9 Hz), 7.60 (1H, dd, J=6.2, 0.9 Hz), 8.26 (1H, d, J=6.2 Hz), 8.58 (1H, d, J=0.9 Hz).

Provenance & Evidence