Sodium hydride → HCID 57561730, compound

HRID 601937Notes

Reaction equation

HRID 601937 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][C:5]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]1=2.[H-].[Na+].[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22]Cl>CN(C=O)C>[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[N:6]([CH2:22][O:21][CH2:20][CH2:19][Si:18]([CH3:25])([CH3:24])[CH3:17])[C:5]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 12464253HCID 12464253, compound

Product 1

HCID 57561730HCID 57561730, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (500 mg, 2.6 mmol) in DMF (3 mL) was added to a cooled (0° C.) suspension of sodium hydride (114 mg, 60% in oil, 2.8 mmol) in DMF (2 mL). After 10 min, 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) (550 μl, 3.1 mmol) was added. The mixture was stirred at rt for 2 h and was then poured into ice-water and extracted with EtOAc. After concentration, methyl 4-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate was obtained as a crude oil (930 mg).

Workup

  1. temperaturea cooled
  2. extractionextracted with EtOAc
  3. concentrationAfter concentration

Sources & evidence

ORD record
ord-b9444611d4b04043aa3b5e87a478e502
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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