Tetrahydrofuran → HCID 89484872, compound
Reaction equation
[C:1](=[O:16])([O-:15])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5](C(C)(C)C)[C:4]=1[F:14].[Li]C[CH2:19][CH2:20][CH3:21].[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[C:31]([N:32]=1)=[CH:30][C:29]([C:33](N(OC)C)=[O:34])=[CH:28][CH:27]=2.[CH2:39]1COCC1>>[C:1](=[O:16])([O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([C:33]([C:29]2[CH:30]=[C:31]3[C:26](=[CH:27][CH:28]=2)[N:25]=[CH:24][C:23]([Cl:22])=[N:32]3)=[O:34])[C:4]=1[F:14])[O:15][C:20]([CH3:19])([CH3:21])[CH3:39]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of tert-butyl(2,4-difluorophenyl) carbonate (2.21 g, 9.6 mmol, 1.2 eq.) in THF (150 mL) cooled at −78° C. was added n-BuLi (3.84 mL, 9.6 mmol, 1.2 eq.) dropwise. The resulting mixture was stirred at −78° C. for 30 min, then a solution of 3-chloro-N-methoxy-N-methylquinoxaline-6-carboxamide (2.0 g, 9.6 mmol, 1.0 eq.) in THF (50 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 1 h, then quenched by the addition of NH4Cl solution. The mixture was extracted with EA (100 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified via flash column chromatography (PE/EA=4/1, v/v) to afford tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4-difluorophenyl) carbonate as a yellow oil (240 mg, 7%).
Workup
- stirringThe resulting mixture was stirred at −78° C. for 1 h
- customquenched by the addition of NH4Cl solution
- extractionThe mixture was extracted with EA (100 mL×3)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified via flash column chromatography (PE/EA=4/1
Sources & evidence
- ORD record
- ord-8c6952dce4f84b898b319a35d5ea0a8d
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249111B2
Reaction notes
Loading…