Chlorosuccinimide → HCID 59633004, compound

HRID 2369039Notes

Reaction equation

HRID 2369039 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28]([OH:31])([CH3:30])[CH3:29])=[N:9]1.[Cl:32]N1C(=O)CCC1=O>CC#N>[Cl:32][C:11]1[C:10]([C:28]([OH:31])([CH3:29])[CH3:30])=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:12]=1[C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:19]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59632719HCID 59632719, compound

Product 1

HCID 59633004HCID 59633004, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 2-{1-(2-Fluoro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazol-3-yl}-propan-2-ol (115 mg, 0.25 mmol) in dry MeCN was added N-chlorosuccinimide (35 mg, 026 mmol) at 20° C. and the reaction mixture was stirred in a sealed vial at 75° C. overnight. Evaporation of solvent gave a residue, which was purified by flash chromatography on silica gel eluting with EtOAC-hexane (0-60%) to afford the title compound as a white solid (123 mg, 100%). 1H-NMR (CDCl3): δ 8.08 (m, 1H), 7.84 (m, 1H), 7.78 (m, 1H), 7.59-7.49 (m, 3H), 7.30-7.28 (m, 2H), 7.17 (t, 1H), 7.03 (d, 1H), 3.08 (s, 4H), 1.74 (s, 6H).

Workup

  1. customEvaporation of solvent
  2. customgave a residue, which
  3. customwas purified by flash chromatography on silica gel eluting with EtOAC-hexane (0-60%)

Sources & evidence

ORD record
ord-b3e07aec90b8474d87af4aed2631632e
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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