Water → HCID 23091904, compound

HRID 1393678Notes

Reaction equation

HRID 1393678 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25].O>CN(C)C=O>[CH3:22][C:23]([CH3:28])([CH3:27])[C:24]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 10264164Benzyl 1H-indole-5-carboxylate

Product 1

HCID 23091904HCID 23091904, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (53 mg) was added to a solution of benzyl 1H-indole-5-carboxylate (276 mg) in N,N-dimethylformamide (2 ml) with ice cooling, and the mixture was stirred for 30 minutes. 2,2-Dimethylpropionyl chloride (162 mg) was added thereto, and the mixture was stirred for 2 hours. Water was added thereto, and the aqueous phase was neutralized, extracted with dichloromethane, and the extract was dried over sodium sulfate anhydrous. The resulting product was concentrated under reduced pressure to give benzyl 1-(2,2-dimethylpropionyl)-1H-indole-5-carboxylate (320 mg, Y.:87%) as pale orange crystals.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionextracted with dichloromethane
  3. dry with materialthe extract was dried over sodium sulfate anhydrous
  4. concentrationThe resulting product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b1d959011a994a1c8e9a8f3151b50f80
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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