Hexachloroethane → HCID 71060343, compound
Reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:16]([C:28]1[O:32][CH:31]=[N:30][CH:29]=1)=[CH:15]2.[Cl:33]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:33][C:31]1[O:32][C:28]([C:16]2[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)=[CH:29][N:30]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
LiHMDS (1.06 M in THF, 3.44 mL, 3.43 mmol) was added to a solution of tert-butyl 5-fluoro-2-(oxazol-5-yl)-1H-indole-1-carboxylate 49 (0.865 g, 2.86 mmol) in THF (20 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of hexachloroethane (1.01 g, 4.29 mmol) in THF (5 mL) was added at −78° C., and the mixture was stirred at −78° C. for 2 h and allowed to warm to room temperature and stirred for 14 h. The reaction was quenched by adding EtOAC: H2O (50 mL: 15 mL), and then extracted with Ethyl acetate. The extracts were washed with brine, dried (Na2SO4) and concentrated. The product was purified by column chromatography (Acetone/hexane as an eluent) to provide tert-butyl 2-(2-chlorooxazol-5-yl)-5-fluoro-1H-indole-1-carboxylate 50 (0.74 g, 77% yield) as white solid. MS (ES) m/z 337 (M+H+).
Workup
- stirringthe mixture was stirred at −78° C. for 2 h
- temperatureto warm to room temperature
- stirringstirred for 14 h
- customThe reaction was quenched
- additionby adding EtOAC
- extractionH2O (50 mL: 15 mL), and then extracted with Ethyl acetate
- washThe extracts were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe product was purified by column chromatography (Acetone/hexane as an eluent)
Sources & evidence
- ORD record
- ord-ef4cc9cac398401aa5872aa765ccbf8d
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865709B2
Reaction notes
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