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

HRID 751502Notes

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-butyldimethylsilyloxy)propyl]-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 pH7 buffer, and extract into ethyl acetate. Combine the organic layers, dry over magnesium sulfate, and concentrate under reduced pressure. Purification by flash chromatography and eluting with ethyl acetate:hexane gradient (100% hexane to 50% ethyl acetate:hexane over 45 minutes) gives the title compound, (4.81 g, 82%) as a clear oil. ESMS (M++1): 318.2 m/z.

Workup

customthe reaction at −78° C. for 30 min
customquench with pH7 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-3a07b45d39c34c53a07a4b6e2021d712
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405305B2

Reaction notes

Loading…