Sodium Acetate → 1-benzenesulfonyl-6-bromo-1H-indol-5-ylmethyl acetate

HRID 221926Notes

Reaction equation

HRID 221926 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:20]Br)=[C:16]([Br:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O-:25])(=[O:24])[CH3:23].[Na+]>CN(C=O)C>[C:22]([O:25][CH2:20][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][C:16]=1[Br:19])[N:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH:11]=[CH:12]2)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 594887781-benzenesulfonyl-6-bromo-5-bromomethyl-1H-indole

Product 1

HCID 594888101-benzenesulfonyl-6-bromo-1H-indol-5-ylmethyl acetateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen stream, to a solution of 1-benzenesulfonyl-6-bromo-5-bromomethyl-1H-indole (14 mg, 0.03 mmol) in DMF (0.2 mL) was added sodium acetate (4 mg, 0.05 mmol), and the resultant mixture was then stirred for 2 hours at 80° C. The reaction mixture was cooled to room temperature, and then purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (2:5)), to thereby obtain the titled compound (11 mg, 85%).

Workup

  1. custompurified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (2:5))

Sources & evidence

ORD record
ord-1d74eaba7a334f4d8b48f1a468afe6bd
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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