Tetrahydrofuran → 4-(Dimethylamino)-N-(2-fluoro-3-formylphenyl)benzamide
Reaction equation
[C:1]([C:3]1[C:4]([F:21])=[C:5]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1)#N.CC(C[AlH]CC(C)C)C.[O:31]1CCCC1>>[CH3:18][N:17]([CH3:19])[C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH:1]=[O:31])[C:4]=2[F:21])=[O:20])=[CH:12][CH:13]=1Participants
4
Conditions
- Temperature
- -78 °C
Procedure
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.
Workup
- temperatureto warm to room temperature
- stirringstirred at room temperature for 4 hr
- stirringstirred at room temperature for 30 min
- extractionThe mixture was extracted with CH2Cl2 (4×100 mL)
- extractionThe combined extract
- filtrationwas filtered through CELITE®
- washwashed with brine (80 mL)
- dry with materialdried over anhydrous MgSO4
- customEvaporation of the solvent under vacuum
Sources & evidence
- ORD record
- ord-0d212403b47f44c2a97af384a3cb84f9
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685969B2
Reaction notes
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