Hydrochloric Acid → (1-benzenesulfonyl-6-bromo-1H-indol-5-yl)methanol

HRID 221927Notes

Reaction equation

HRID 221927 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:14]=1[Br:15])[N:11]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:10]=[CH:9]2)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[C:19]1([S:16]([N:11]2[C:12]3[C:8](=[CH:7][C:6]([CH2:5][OH:4])=[C:14]([Br:15])[CH:13]=3)[CH:9]=[CH:10]2)(=[O:17])=[O:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 594888101-benzenesulfonyl-6-bromo-1H-indol-5-ylmethyl acetate

Product 1

HCID 59488751(1-benzenesulfonyl-6-bromo-1H-indol-5-yl)methanolYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen stream, a mixture of 1-benzenesulfonyl-6-bromo-1H-indol-5-ylmethyl acetate (257 mg, 0.63 mmol), potassium carbonate (15 mg, 0.11 mmol) and methanol (4 mL) was stirred for 1 hour at room temperature. To the resultant mixture was added 2 N hydrochloric acid (0.11 mL), and solvent was then removed by distillation under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (2:1)), to thereby obtain the titled compound (225 mg, 97%).

Workup

  1. customwas then removed by distillation under reduced pressure
  2. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (2:1))

Sources & evidence

ORD record
ord-8dcaee1db5db447cab54748e41394588
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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