Sodium hydride → 4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

A flask was charged with 4-chloro-1H-pyrrolo[2,3-b]pyridine (6.0 g, 39 mmol, Arkpharm) and THF (100 mL). The mixture was cooled to about 0° C. and 60 wt % NaH (1.89 g, 47.2 mmol) was added portion-wise. The mixture was warmed to rt and after about 45 min. TIPSCl (12.5 mL, 59.0 mmol) was added drop-wise and mixture was allowed to stir overnight at rt. The mixture was quenched with water (100 mL) and extracted with EtOAc (200 mL). The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography with a gradient of 0 to 10% EtOAc/heptane to give 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (11.0 g, 91%): 1H NMR (d-DMSO) δ 8.20 (d, J=5.17 Hz, 1H), 7.59 (d, J=3.55 Hz, 1H), 7.23 (d, J=5.16 Hz, 1H), 6.68 (d, J=3.50 Hz, 1H), 1.83 (m, 3H), 1.06 (m, 18H).

Provenance & Evidence