Sodium hydride → 1-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-indole-7-carbonitrile

HRID 63060Notes

Reaction equation

HRID 63060 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)#[N:2].[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:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[C:1]#[N:2])[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 108988161H-Indole-7-carbonitrile

Product 1

HCID 867282061-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-indole-7-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Cyanoindole (1.0 g, 7.0 mmol) was stirred in DMF (10 mL) at 0° C. Sodium hydride (60%, 310 mg, 7.7 mmol) was added, and the reaction stirred 30 min at rt. SEM-chloride was added, and the reaction stirred 16 h. The solution was concentrated in vacuo and purified by silica gel chromatography (10-40% EtOAc/hexanes) to give 1.5 g (78%) of the title compound as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.85 (dd, 1H, J=7.9, 0.9 Hz), 7.56 (d, 1H, J=7.5 Hz), 7.26 (d, 1H, J=6.3 Hz), 7.17 (t, 1H, J=7.7 Hz), 6.62 (d, 1H, J=3.3 Hz), 5.79 (s, 2H), 3.58 (t, 2H, J=8.1 Hz), 0.92 (t, 2H, J=8.2 Hz), −0.05 (s, 9H). [M+H] calc'd for C15H20N2OSi, 273. found 273.

Workup

  1. stirringthe reaction stirred 16 h
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by silica gel chromatography (10-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c9432adbc775442e9a48aab49de10f94
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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