Sodium hydride → HCID 68682445, compound

HRID 1715311Notes

Reaction equation

HRID 1715311 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[N:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][C:25]2=[O:29])[NH:19][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:17]3)=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH3:36][Si:37]([CH3:44])([CH3:43])[CH2:38][CH2:39][O:40][CH2:41]Cl.[Cl-].[NH4+]>CN(C)C=O>[CH3:3][S:4]([C:7]1[N:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][C:25]2=[O:29])[N:19]([CH2:41][O:40][CH2:39][CH2:38][Si:37]([CH3:44])([CH3:43])[CH3:36])[C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:17]3)=[CH:9][CH:8]=1)(=[O:6])=[O:5]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 57687003HCID 57687003, compound

Product 1

HCID 68682445HCID 68682445, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With cooling with ice, sodium hydride (30% liquid paraffin added) (6 mg) was added to an N,N-dimethylformamide (2 ml) solution of the indole compound (50 mg) obtained in Example 3, then 2-(trimethylsilyl)ethoxy methyl chloride (24 mg) was added, and stirred at room temperature for 1 hour. With cooling with ice, aqueous saturated ammonium chloride solution was added, then extracted with ethyl acetate, and the organic layer was washed with water and saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified by partitioning reversed-phase liquid chromatography to obtain the entitled compound.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated saline water
  4. customAfter dried
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe residue was purified
  7. customby partitioning reversed-phase liquid chromatography
  8. customto obtain the entitled compound

Sources & evidence

ORD record
ord-773556b4c86547b49bb829ca3b0a8e22
Source dataset
uspto-grants-2010_09
Patent number
US07799820B2

Reaction notes

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