1H-Pyrrolo[2,3-b]pyridine, 5-broMo-2,3-dihydro-3-Methyl- synthesis

Yield: 94.9%

Reaction Conditions:

with sodium hydroxide;ethanol;water at 100; for 5 h;

Steps:

5
Step 5: To a stirring solution of compound 61 (800 mg, 2.26 mmol) in 10 ml_ of boiling ethanol was added 2.0 mL aqueous solution of sodium hydroxide (127 mg, 2.26 mmol) dropwise. The reaction was sealed then heated in 100 degree oil bath and monitored with LCMS. Reaction stayed homogenous and 5 hours later, LCMS indicated reaction complete. Reaction was concentrated to dryness under high vacuum. The resulting residual was stirred in 100 mL DCM overnight and then filtered. LCMS indicated the solids contained no desired material while the filtrate was concentrated to give compound 62 (458 mg, 94.9%) as an off-white solid.

References:

PFIZER INC. WO2009/16460, 2009, A2 Location in patent:Page/Page column 49-50