Tetrahydrofuran → HCID 89484871, 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].CON(C)[C:25]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][CH:31]=[N:30]2)=[O:26].[CH2:38]1COCC1>>[C:1](=[O:16])([O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([C:25]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[N:33]=[CH:32][CH:31]=[N:30]3)=[O:26])[C:4]=1[F:14])[O:15][C:20]([CH3:19])([CH3:21])[CH3:38]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of tert-butyl(2,4-difluorophenyl) carbonate (2.3 g, 10 mmol, 1.2 eq.) in THF (50 mL) cooled at −78° C. was added n-BuLi (6.25 mL, 15 mmol, 1.8 eq.) dropwise. The resulting mixture was stirred at −78° C. for 30 min, then a solution of N-methoxy-N-methylquinoxaline-6-carboxamide (1.8 g, 8.7 mmol, 1.0 eq.) in THF (20 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 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified via flash column (PE/EA=3/1, v/v) to afford tert-butyl (2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl) carbonate as yellow foam (1.06 g, 30.3%).
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 (50 mL×3)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated
- customThe residue was purified via flash column (PE/EA=3/1
Sources & evidence
- ORD record
- ord-21b8d4ed00bd47358b6e8ae6f88afb1e
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249111B2
Reaction notes
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