Sodium hydride → HCID 67187975, compound

HRID 1695210Notes

Reaction equation

HRID 1695210 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH:16]([Si:19]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])Cl)([CH3:18])[CH3:17]>CN(C=O)C>[CH3:13][O:12][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([Si:19]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:16]([CH3:18])[CH3:17])[CH:2]=[CH:3]2)=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 67187975HCID 67187975, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g of methyl indole-5-carboxylate (5.7 mmol) in 10 mL of dry DMF 273 mg of NaH (mineral oil dispersion 50-60%, 5.7 mmol) were added and the mixture cooled to 0° C. Triisopropylchlorosilane (1.06 g, 5.7 mmol) were added drop wise and after 1 hour LC-MS showed complete conversion of the starting material to the title product. The mixture was diluted with 30 mL of DCM and washed with saturated Na2CO3. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude was purified with SiO2 column eluting with n-hexane. The title compound was obtained (500 mg, yield 26%)

Sources & evidence

ORD record
ord-abf2cd3ce8fa4d3d84eeb677a1ad05b9
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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