Phenacyl bromide → HCID 71237789, compound

HRID 1409679Notes

Reaction equation

HRID 1409679 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([C@@H:13]3[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]3[C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C@@H:13]3[CH2:18][CH2:17][N:16]([CH2:27][C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:29])[CH2:15][C@H:14]3[C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[NH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 178505751HCID 178505751, compound

Product 1

HCID 71237789HCID 71237789, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3R,4R)-4-[5-(4-chlorophenyl)-1H-pyrazol-3-yl]-3-(4-fluorophenyl)piperidine (100 mg, 0.213 mmol, prepared in a similar manner to Examples 7 and 8), 2-bromoaceto-phenone (50.8 mg, 0.255 mmol) and potassium carbonate (147 mg, 1.064 mmol) in acetonitrile (1.0 ml) was stirred at rt for 4 h. Direct purification of the crude reaction mixture by RP-HPLC (C18, acetonitrile, water, 0.1% TFA) afforded the title compound. HPLC/MS: 474.3, 476.3 (M+1); Rt=1.74 min (LC-4 HPLC conditions).

Workup

  1. customDirect purification of the crude
  2. customreaction mixture by RP-HPLC (C18, acetonitrile, water, 0.1% TFA)

Sources & evidence

ORD record
ord-a59a7c7aa426431ca6f4d8d2ebfbc4c5
Source dataset
uspto-grants-2014_12
Patent number
US08921394B2

Reaction notes

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