Acetonitrile → HCID 22228532, compound

HRID 1173103Notes

Reaction equation

HRID 1173103 reaction equation
[Si]([O:8][C:9]1[CH:17]=[CH:16][C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)(=[O:21])=[O:20])=[C:14]2[C:10]=1[C:11]([Cl:29])=[CH:12][NH:13]2)(C(C)(C)C)(C)C.F.C(#N)C>O>[Cl:28][C:24]1[CH:23]=[C:22]([S:19]([NH:18][C:15]2[CH:16]=[CH:17][C:9]([OH:8])=[C:10]3[C:14]=2[NH:13][CH:12]=[C:11]3[Cl:29])(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14917Hydrofluoric AcidHCID 19080181HCID 19080181, compound

Product 1

HCID 22228532HCID 22228532, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

220 mg (0.47 mmol) of N-(4-tert-butyldimethylsilyloxy-3-chloro-1H-indole-7-yl)-3-chlorobenzenesulfonamide synthesized in the same manner as in Synthetic Example 1a was added to a mixed solution (2 ml) of an aqueous 40% hydrogen fluoride solution/acetonitrile (1:10). After stirred at room temperature overnight, water was added thereto and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 141 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c8137974157405684dd537dcce4c7b5
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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