3,4-Dichlorobenzyl chloride → HCID 22718721, compound

HRID 1582644Notes

Reaction equation

HRID 1582644 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([Cl:17])[C:13]([O:18][CH3:19])=[CH:12][CH:11]=2)=[O:7])[CH3:4].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24]Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:24][C:23]2[CH:26]=[CH:27][C:28]([Cl:29])=[C:21]([Cl:20])[CH:22]=2)[C:10]2[C:15]([CH:16]=1)=[C:14]([Cl:17])[C:13]([O:18][CH3:19])=[CH:12][CH:11]=2)=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 22718731HCID 22718731, compound

Product 1

HCID 22718721HCID 22718721, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60 mg) was added to a solution of ethyl-4-chloro-5-methoxyindole-2-carboxylate (250 mg), 3,4-dichlorobenzylchloride (0.21 ml) and tetrabutylammoniumiodide (3 mg) in DMF at ambient temperature under an inert atmosphere. The reaction was stirred at ambient temperature for 18 hours then partitioned between ethylacetate (30 ml) and water(30 ml). The organic phase was dried (MgSO4), concentrated under vacuo and the residue purified by column chromatography using isohexane-15% ethylacetate as eluent to yield the product as a white solid (196 mg,48%) NMR: δ (CDCl3) 1.39 (t, 3H), 3.93 (s, 3H), 4.32 (q, 2H), 5.73(s, 2H), 6.84 (dd, iH), 7.06-7.16 (m, 3H), 7.31 (d, 1H), 7.42 (s, 1H)

Workup

  1. customthen partitioned between ethylacetate (30 ml) and water(30 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under vacuo
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-06f91490c77a49139bf9ecfe558b302f
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

Loading…