Trimethylsilyl iodide → 4-(6-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-4-ol

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Reaction Conditions

Reaction Steps

To tert-butyl 4-(6-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-4-hydroxypiperidine-1-carboxylate (510 mg, 1.00 mmol) in CH2Cl2 (6 mL) was slowly dropwise added TMS-I (0.43 mL, 3.01 mmol) at rt, and stirred at 60° C. overnight. Partial of the solvent was removed on rotary vacuo, and the residue was purified on reverse phase PrepHPLC to afford the expected product, 4-(6-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-4-ol (310 mg, 63%), as a dark brown solid. 1H-NMR (400 MHz, CHLOROFORM-D) δ ppm 2.02 (d, J=14.35 Hz, 2 H) 2.65-2.76 (m, 2 H) 3.42 (d, J=11.33 Hz, 2 H) 3.58 (d, J=11.83 Hz, 2 H) 4.61 (s, 2 H) 6.91 (d, J=3.53 Hz, 1 H) 7.13 (s, 1 H) 7.28 (d, J=3.53 Hz, 1 H); Mass spec. 252.05 (MH+) calc. for C12H14ClN3O 251.08.

Provenance & Evidence