Methanol → HCID 71074609, compound

HRID 1851890Notes

Reaction equation

HRID 1851890 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1.[H-].[Na+].CO>CN(C=O)C>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 71074609HCID 71074609, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1H-indole-5-carboxylate (1.09 g, 6.2 mmol, 1 equiv) and 1-(bromomethyl)-4-bromobenzene (1.70 g, 6.82 mmol, 1.1 equiv) in anhydrous DMF (30 mL) under argon atmosphere was added sodium hydride (500 mg, 12.4 mmol, 2 equiv) in small portions. The mixture was stirred 2 h at room temperature. The reaction mixture was then neutralized by addition of methanol and concentrated in vacuo. The residue was dissolved in AcOEt, washed with brine and dried over MgSO4. The crude was purified by flash chromatography (Hexane/AcOEt 7.5/2.5) to afford the title compound as a white powder (1.09 g, 3.2 mmol, 52%). ESI-MS (m/z): 344/346 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude was purified by flash chromatography (Hexane/AcOEt 7.5/2.5)

Sources & evidence

ORD record
ord-4d1788964f6b4b03baaeed9e21b9a512
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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