N-bromobutanimide → HCID 59251421, compound

HRID 1046644Notes

Reaction equation

HRID 1046644 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([C:22]([OH:25])([CH3:24])[CH3:23])[N:19]=[C:18]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[Br:36]N1C(=O)CCC1=O>CC#N.CCOC(C)=O>[Br:36][C:21]1[N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=3)=[CH:12][CH:13]=2)[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])=[N:19][C:20]=1[C:22]([OH:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59251380HCID 59251380, compound

Product 1

HCID 59251421HCID 59251421, compoundYield 86,291.898%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[1-(3′-methanesulfonyl-biphenyl-4-yl)-2-(2-trifluoromethyl-phenyl)-1H-imidazol-4-yl]-propan-2-ol (100 mg, 0.20 mmol) in MeCN (2 mL, anhyd) was added N-bromosuccinimide (45 mg, 0.25 mmol). After 2 h, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3, water (3×10 mL) and brine, then dried (Na2SO4) and concentrated. The residue was purified by chromatography (silica), eluting with EtOAc/hexanes (65:40 to 95:5) to yield the title compound (100 g, 86%) as a white solid. 1H-NMR (CD2Cl2): δ 8.10 (1H, m), 7.92 (1H, m), 7.86 (1H, m), 7.60-7.74 (4H, m), 7.47 (2H, m), 7.25-7.31 (3H, m), 3.56 (1H, s), 3.06 (3H, s), 1.66 (6H, s); MS (ES): 579, 581 [M+H]+.

Workup

  1. washwashed with saturated NaHCO3, water (3×10 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (silica)
  5. washeluting with EtOAc/hexanes (65:40 to 95:5)

Sources & evidence

ORD record
ord-14eefaf1983d47adbc201fbb2c3e3eb5
Source dataset
uspto-grants-2013_10
Patent number
US08569352B2

Reaction notes

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