Dimethylformamide → 1-[3-(tert-Butyldimethylsilyloxy)propyl]-1H-indole-4-carboxaldehyde

HRID 557181Notes

Reaction equation

C([Li])(C)(C)C.Br[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[CH2:16][CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].CN(C)[CH:29]=[O:30]>O1CCCC1>[Si:20]([O:19][CH2:18][CH2:17][CH2:16][N:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:7]([CH:29]=[O:30])[C:8]=2[CH:9]=[CH:10]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Add tert-butyl lithium (27.07 ml, 46.03 mmol, 1.7 M in pentane) to a solution of 4-Bromo-1-[3-(tert-butyldimethyl-silyloxy)prop-1-yl]-1H-indole (6.76 g, 18.41 mmol) in anhydrous tetrahydrofuran (100 ml) at −78° C. Stir the reaction at −78° C. for 30 min, quench with N,N-dimethylformamide (4.7 ml, 64.45 mmol), warm to 0° C., quench with pH=7 buffer, and extract into ethyl acetate. Combine the organic layers, dry over magnesium sulfate, and concentrate under reduced pressure. Purification by flash chromatography, eluting with ethyl acetate:hexane gradient (100% hexane to 50% ethyl acetate:hexane over 45 minutes) gives the title compound as a clear oil.

Workup

customthe reaction at −78° C. for 30 min
customquench with pH=7 buffer
extractionextract into ethyl acetate
dry with materialdry over magnesium sulfate
concentrationconcentrate under reduced pressure
customPurification by flash chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-da5f6b04630d4b5ebbe11ce613ffc20d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058425B2

Reaction notes

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