Hexachloroethane → Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-yl ester

HRID 1971409Notes

Reaction equation

[C:1]([Si:5]([CH3:24])([CH3:23])[N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.C([Li])(CC)C.[Cl:38]C(Cl)(Cl)C(Cl)(Cl)Cl.[Cl-].[NH4+]>C1COCC1>[C:1]([Si:5]([CH3:24])([CH3:23])[N:6]1[C:14]2[C:9](=[C:10]([Cl:38])[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl ester (9.26 g, 26.7 mmol) is dissolved in THF (250 mL), flushed with nitrogen and cooled to −78° C. TMEDA (5 mL, 33.1 mmol) is then added followed by sec-butyllithium (24.8 mL, 34.7 mmol) and the reaction is stirred for 30 minutes. Hexachloroethane (12.73 g, 53.8 mmol) in 50 mL of THF is added over 10 minutes to the reaction. The reaction is allowed to warm to room temperature overnight (15 hours). The reaction is cooled using an ice bath and a saturated ammonium chloride (aq) solution is added (150 mL). The mixture is then extracted with ethyl acetate, dried (sodium sulfate) and concentrated to obtain the title compound as an oil that is used without further purification. MS (ESI) m/z 381.1 (M+1).

Workup

customflushed with nitrogen
temperatureto warm to room temperature overnight (15 hours)
temperatureThe reaction is cooled
extractionThe mixture is then extracted with ethyl acetate
dry with materialdried (sodium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-3727f4d0ba2d4af8a1e24decc52d97d3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431584B2

Reaction notes

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