Tetrahydrofuran → 4-(Dimethylamino)-N-(2-fluoro-3-formylphenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-cyano-2-fluorophenyl)-4-(dimethylamino)benzamide (2.18 g, 7.70 mmol) in tetrahydrofuran (150 mL) at −78° C. was added DIBAL-H (23.09 mL, 23.09 mmol) over 20 min. The mixture was stirred at −78° C. for 1 h before it was allowed to warm to room temperature and stirred at room temperature for 4 hr. The mixture was poured into ice/water (600 mL) and stirred at room temperature for 30 min. The mixture was extracted with CH2Cl2 (4×100 mL). The combined extract was filtered through CELITE®, washed with brine (80 mL), and dried over anhydrous MgSO4. Evaporation of the solvent under vacuum provided a crude product (1.83 g) as a pale yellow solid. This product was used in the next step without further purification.

Provenance & Evidence