3,4-Dichlorobenzyl chloride → HCID 22718719, compound

HRID 1582640Notes

Reaction equation

HRID 1582640 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([F:16])[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:11][CH:10]=2)=[O:6].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:29]Cl>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[N:8]([CH2:29][C:28]2[CH:31]=[CH:32][C:33]([Cl:34])=[C:26]([Cl:25])[CH:27]=2)[C:9]2[C:14]([CH:15]=1)=[C:13]([F:16])[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:11][CH:10]=2)=[O:6]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 22718738HCID 22718738, compound

Product 1

HCID 22718719HCID 22718719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 589 mg) was added to a solution of methyl-4-fluoro-5-benzyloxyindole-2-carboxylate (4 g) in dimethylformamide (100 ml) and the mixture was stirred under an argon atmosphere for 30 minutes. 3,4-dichlorobenzyl chloride (2.22 ml) was added and the mixture stirred overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between diethyl ether (100 ml) and water (100 ml). Organic extracts were washed with water (100 ml), dried (MgSO4), concentrated in vacuo and purified by flash column chromatography; using iso-hexane followed by 5% ethyl acetate/iso-hexane as eluent, to give the product as a yellow crystalline solid (4.61 g) 1H NMR (DMSO-d6) δ 3.80(s, 3H), 5.15(s, 2H), 5.80(s, 2H), 6.85(m, 1H), 7.25-7.52(m, 10H); M/z(+) 458.2 (MH+)

Workup

  1. stirringthe mixture stirred overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between diethyl ether (100 ml) and water (100 ml)
  4. washOrganic extracts were washed with water (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-929c14589cf04c158f1c8a0a157370cd
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

Loading…