Potassium Carbonate → HCID 76283451, compound

HRID 522312Notes

Reaction equation

HRID 522312 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[N:10][N:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:12]=2[CH3:13])[C:3]1=[O:21].[Cl:22][C:23]1[C:24]([C:29]([F:32])([F:31])[F:30])=[N:25][NH:26][C:27]=1[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:22][C:23]1[C:24]([C:29]([F:31])([F:30])[F:32])=[N:25][N:26]([CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]3[CH:9]=[N:10][N:11]([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=4)[C:12]=3[CH3:13])[C:3]2=[O:21])[C:27]=1[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12069654-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazoleHCID 86723025HCID 86723025, compound

Product 1

HCID 76283451HCID 76283451, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-1-[1-(4-fluorophenyl)-5-methylpyrazol-4-yl]piperidin-2-one (0.05 g, 0.14 mmol) in DMF (1.0 mL) was added 4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazole (0.031 g, 0.17 mmol), followed by potassium carbonate (0.029 g, 0.21 mmol). After stirring at room temperature for 1 h, the reaction was quenched with water. The aqueous layer was then extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the title compound as a white solid (0.015 g, 0.025 mmol, 23%). 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.44-7.35 (m, 2H), 7.22-7.13 (m, 2H), 4.94 (dd, J=9.9, 6.3 Hz, 1H), 3.90-3.70 (m, 2H), 2.73 (dddd, J=13.2, 11.5, 9.8, 3.3 Hz, I H), 2.47-2.38 (m, 1H), 2.36 (s, 3H), 2.31 (ddd, J=10.6, 5.4, 2.4 Hz, 1H), 2.17-2.12 (m, 1H), 2.13 (s, 3H); MS: (ES) m/z calculated for C20H18ClF4N5O [M+H]+ 456.1. found 456.1.

Workup

  1. customthe reaction was quenched with water
  2. extractionThe aqueous layer was then extracted with ethyl acetate (2×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-3e2e3fc364834ceaa2852cb2b3c23c3e
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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