Sodium Chloride → 4-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)morpholine

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Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (800 mg, 2.26 mmol, Eq: 1.00), palladium (II) acetate (254 mg, 1.13 mmol, Eq: 0.5) and tri-tert-butylphosphine (229 mg, 279 μl, 1.13 mmol, Eq: 0.5) were combined with toluene to give a yellow solution. Morpholine (789 mg, 789 μl, 9.06 mmol, Eq: 4) and sodium tert-butoxide (653 mg, 6.79 mmol, Eq: 3) were added. The reaction mixture was heated to 80° C. and stirred for 1 h. The reaction mixture was poured into 20 mL sat NaCl and extracted with EtOAc (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 80 g, 10% to 15% EtOAc in hexanes) to give 4-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)morpholine (703 mg, 86%) as a light brown oil.

Provenance & Evidence