Sodium hydride → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-6-carbonitrile

HRID 2174092Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:14][Si:15]([CH2:18][CH2:19][O:20][CH2:21]Cl)([CH3:17])[CH3:16]>CN(C=O)C>[CH3:14][Si:15]([CH3:17])([CH3:16])[CH2:18][CH2:19][O:20][CH2:21][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

1H-Indole-6-carbonitrile (CAS #:15861-36-6) (1.47 g, 10.34 mmol) was dissolved in DMF (103 mL) and cooled to 0° C. NaH (60% in mineral oil, 0.620 g, 15.51 mmol) was added in one batch. The reaction was allowed to stir at room temperature for 15 minutes. SEMCl (2.38 mL, 13.44 mmol) was added at 0° C. and stirred for 20 minutes. The reaction was quenched with saturated ammonium chloride and then EtOAc was added. The organic layer was removed and the water layer was extracted again with EtOAc. The combined organics were washed with water, dried over MgSO4 filtered and concentrated. The resulting residue was purified via flash chromatography (0-50% EtOAc:heptanes) to obtain title compound. MS (ESI+) m/z 273.23 (M+H).

Workup

stirringstirred for 20 minutes
customThe reaction was quenched with saturated ammonium chloride
additionEtOAc was added
customThe organic layer was removed
extractionthe water layer was extracted again with EtOAc
washThe combined organics were washed with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified via flash chromatography (0-50% EtOAc:heptanes)

Sources & evidence

ORD record: ord-294edd161127410d86008863fae613a8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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