Cesium carbonate → HCID 68052780, compound

HRID 1685135Notes

Reaction equation

HRID 1685135 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[C:11]([C:23]([O-:25])=[O:24])[N:10]([CH3:26])[N:9]=2)=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]1=[O:33].[C:34](=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][C:28]4=[O:33])=[CH:3][CH:4]=3)=[N:9][N:10]([CH3:26])[C:11]=2[C:23]([O:25][CH3:34])=[O:24])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 126652-PiperidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86651931HCID 86651931, compound

Product 1

HCID 68052780HCID 68052780, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(4-bromophenyl)-4-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-5-carboxylate T-12 (0.5 g, 1.2 mmol) in anhydrous 1,4-dioxane (10 mL) under nitrogen were added 2-piperidone (0.17 g, 1.7 mmol), cesium carbonate (0.755 g, 2.3 mmol), Xantphos (0.15 g, 0.26 mmol) and Pd2dba3 (0.05 g, 0.055 mmol). The reaction mixture was heated in a microwave reactor at 120° C. for 1 hour. The reaction mixture was filtered and washed with dichloromethane and ethyl acetate. The filtrate was evaporated under reduced pressure. The residue was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to afford the desired methyl 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazole-5-carboxylate T-21 (0.44 g, 1.0 mmol).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with dichloromethane and ethyl acetate
  3. customThe filtrate was evaporated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customSolvent was evaporated under reduced pressure
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f759c3ec9a9c4357a293c4abeb6bd966
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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