Water → HCID 22987966, compound
Reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.CON(C)[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1.O>O1CCCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([C:13]2[CH:12]=[N:11][CH:10]=[CH:9][C:8]=2[NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:30])=[CH:24][CH:25]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-pivaloylaminopyridine (7.0 g, 39 mmol) in tetrahydrofuran (100 ml) was added n-butyllithium (39.3 ml, 98 mmol, 2.5 M solution in tetrahydrofuran) at −78° C. under a N2 atmosphere. The reaction mixture was stirred at 0° C. for 5 h, re-cooled to −78° C. and quenched with a solution of N-methoxy-N-methyl-4-fluorobenzamide (7.9 g, 43 mmol) in 100 ml tetrahydrofuran. The reaction mixture was warmed to room temperature and poured into water. The product was extracted into ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography (10% ethyl acetate/hexanes gradient) to afford N-[3-(4-fluorobenzoyl)-pyridin-4-yl]-2,2-dimethylpropanamide (10 g).
Workup
- temperaturere-cooled to −78° C.
- temperatureThe reaction mixture was warmed to room temperature
- extractionThe product was extracted into ethyl acetate
- washThe organic layers were washed with brine
- dry with materialdried over sodium sulfate
- customevaporated to dryness
- customThe residue was purified by flash chromatography (10% ethyl acetate/hexanes gradient)
Sources & evidence
- ORD record
- ord-ad7a305486374d128ae21c5e9000ae17
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479507B2
Reaction notes
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