Quinoxaline-6-carboxaldehyde → HCID 89462621, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].[Li]CCCC.[N:21]1[C:30]2[C:25](=[CH:26][C:27]([CH:31]=[O:32])=[CH:28][CH:29]=2)[N:24]=[CH:23][CH:22]=1>C1COCC1>[F:1][C:2]1[C:7]([CH:31]([OH:32])[C:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[N:21]=[CH:22][CH:23]=[N:24]3)=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of N-(2,4-difluorophenyl)pivalamide (740 mg, 3.46 mmol, 1.2 eq.) in THF (10 mL) cooled at −78° C. was added n-BuLi (2.76 mL, 6.9 mmol, 2.4 eq.) dropwise. The resulting mixture was stirred at −78° C. for 1 h, then a solution of quinoxaline-6-carbaldehyde (450 mg, 2.88 mmol, 1.0 eq.) in THF (20 mL) was added dropwise. The mixture was stirred at −78° C. for 1 h, then quenched by the addition of NH4Cl solution. The mixture was extracted with EA (20 mL×3) and the combined organic layers were dried over Na2SO4 and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=2/1, v/v) to afford N-(2,4-difluoro-3-(hydroxy(quinoxalin-6-yl)methyl)phenyl)pivalamide as a yellow foam (541 mg, 50.7%).
Workup
- stirringThe mixture was stirred at −78° C. for 1 h
- customquenched by the addition of NH4Cl solution
- extractionThe mixture was extracted with EA (20 mL×3)
- dry with materialthe combined organic layers were dried over Na2SO4
- concentrationconcentrated
- customThe resulting residue was purified via flash column chromatography (PE/EA=2/1
Sources & evidence
- ORD record
- ord-65df5b16a4b04175a9b8099ac1dcf0ac
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249110B2
Reaction notes
Loading…