3-Bromo-1-propanol → HCID 18522143, compound

HRID 413796Notes

Reaction equation

HRID 413796 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([SH:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH:27][CH2:28][CH2:29][CH2:30]Br>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([S:17][CH2:30][CH2:29][CH2:28][OH:27])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 18522134HCID 18522134, compound

Product 1

HCID 18522143HCID 18522143, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (20 mg) was added to a stirred solution of ethyl N-(3,4-dichlorobenzyl)-4-mercaptoindole-2-carboxylate (170 mg) in DMF (7.5 ml). After 1 hour, 3-hydroxyprop-1-yl bromide (89 mg) was added and stirring continued for 16 hours. The reaction mixture was partitioned between water and ethyl acetate and combined organic extracts were dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using dichloromethane as eluent to give the product as a yellow gum (30 mg, 14%); M/z (+) 480.1 (MH+).

Workup

  1. waitcontinued for 16 hours
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialwere dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-58699ac5415040698cdbf4889c3223be
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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