Hexachloroethane → tert-butyl 2-(2-chlorooxazol-5-yl)-1H-indole-1-carboxylate
Reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[O:11]1[C:15]([C:16]2[N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][N:13]=[CH:12]1.[Cl:32]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:32][C:12]1[O:11][C:15]([C:16]2[N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][N:13]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
LiHMDS (1.06 M in THF, 9.54 mL, 10.00 mmol) was added to a solution of tert-butyl 2-(oxazol-5-yl)-1H-indole-1-carboxylate 20 (2.37 g, 8.34 mmol) in THF (20 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of hexachloroethane (2.96 g, 12.50 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)-1H-indole-1-carboxylate 21 (2.64 g, 99% yield) as white solid. MS (ES) m/z 319 (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-0e55799e16f0453297a1c06e2771c461
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865709B2
Reaction notes
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