Water → 1-(5-Chloro-1,1-dioxo-1H-1lambda6-thiophen-2-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

HRID 244426Notes

Reaction equation

HRID 244426 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[N:17]=[CH:16]3)([OH:12])[C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.[OH2:40]>C(Cl)Cl>[Cl:1][C:2]1[S:6](=[O:37])(=[O:40])[C:5]([C:7]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[N:17]=[CH:16]3)([OH:12])[C:8]([F:10])([F:11])[F:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 249620151-(5-Chlorothiophen-2-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

Product 1

HCID 594372551-(5-Chloro-1,1-dioxo-1H-1lambda6-thiophen-2-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanolYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 100 mg (0.2 mmol) of 1-(5-chlorothiophen-2-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol in 5 mL of CH2Cl2 was added 100 mg (0.5 mmol) of m-chloroperbenzoic acid. After 3 hours, the reaction was diluted with 5 mL of water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate in hexanes (10-30% gradient) to afford 14 mg (13%) of the title compound. MS m/z 459.82 (MH+).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c8d1620f18984441a3a811360a94c993
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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