N-bromobutanimide → HCID 59632711, compound

HRID 2369038Notes

Reaction equation

HRID 2369038 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:29])[F:28])[N:19]=[C:18]([C:31]([OH:34])([CH3:33])[CH3:32])[CH:17]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[Br:35]N1C(=O)CCC1=O>CC#N>[Br:35][C:17]1[C:18]([C:31]([OH:34])([CH3:32])[CH3:33])=[N:19][N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:28])[F:29])[C:16]=1[C:14]1[S:15][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59632067HCID 59632067, compound

Product 1

HCID 59632711HCID 59632711, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2-[5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1-(2-trifluoromethyl-phenyl)-1H-pyrazol-3-yl]-propan-2-ol (254 mg, 0.5 mmol) in dry MeCN was added N-bromosuccinimide (94 mg, 0.53 mmol) at 20° C. and the reaction mixture was stirred at 20° C. overnight. Evaporation of solvent gave a residue, which was purified by flash chromatography on silica gel eluted with EtOAC-hexane (0-60%) to afford the title compound as a white solid (286 mg, 98%). 1H-NMR (CDCl3): δ 8.05 (m, 1H), 7.85-7.81 (m, 2H), 7.76 (m, 1H), 7.63-7.61 (m, 2H), 7.56 (t, 1H), 7.39 (m, 1H), 7.25 (d, 1H), 6.98 (d, 1H), 3.09 (s, 1H), 3.07 (s, 3H), 1.74 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-b3d61f94ecb3439fba6f6ee4872429b3
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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