Water → HCID 57683248, compound

HRID 1864971Notes

Reaction equation

HRID 1864971 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)([O-:5])=[O:4].[CH2:15]([O:17][C:18](=[O:21])[CH2:19]Br)[CH3:16].O>CN(C)C=O>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][N:10]1[C:11]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indole

Product 1

HCID 57683248HCID 57683248, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%/mineral oil: 81 mg) was dissolved in dimethylformamide (5 mL), and the solution was cooled to 0° C. After addition of 4-nitroindole (300 mg), the mixture was stirred for one hour, and bromoacetic acid ethyl ester (340 mg) was added thereto, followed by stirring at 0° C. for 4 hours. Water was added thereto and the mixture was concentrated, diluted with ethyl acetate, washed with water, dried over sodium sulfate, then concentrated to give the title compound (367 mg)

Workup

  1. stirringby stirring at 0° C. for 4 hours
  2. concentrationthe mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a95e0e63f60e41a8ac385c7802dc677f
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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