Sodium hydride → HCID 86612915, compound

HRID 1445888Notes

Reaction equation

HRID 1445888 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:24])[CH2:12][O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:23])[NH:18]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:25][CH:26](Br)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:10][C:11](=[O:24])[CH2:12][O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:23])[N:18]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][Br:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 113249061,1-DibromododecaneHCID 58765424(2-Methyl-1H-indol-4-yloxy)-acetic acid benzyl ester

Product 1

HCID 86612915HCID 86612915, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 0.093 g, 6.45 mmole) in DMF (10 mL), (2-methyl-1H-indol-4-yloxy)-acetic acid benzyl ester (2) (0.845 g, 2.3 mmole) was added. The mixture was stirred at room temperature for 1 h. To the mixture, dibromododecane (0.765 g, 2.3 mmole) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate and washed with water. The organic layer was separated, dried with sodium sulphate and concentrated. The residue was purified by column chromatography (10:1, hexane: EtOAc) to afford intermediate 3. Yield: 0.708 g, 45%.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 18 h
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (10:1, hexane: EtOAc)

Sources & evidence

ORD record
ord-e4ca5912b9f34cb28c09fa906118453e
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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