Water → HCID 86692601, compound

HRID 1748661Notes

Reaction equation

HRID 1748661 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:28]1[N:33]=[CH:32][C:31]([NH:34][C:35]([C:37]2[CH:38]=[N:39][N:40]([C:43]3[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][N:44]=3)[C:41]=2[CH3:42])=[O:36])=[CH:30][C:29]=1[CH3:53]>O1CCOCC1.C(OCC)(=O)C>[CH3:42][C:41]1[N:40]([C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:50])([F:52])[F:51])=[CH:45][N:44]=2)[N:39]=[CH:38][C:37]=1[C:35]([NH:34][C:31]1[CH:32]=[N:33][C:28]([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([F:16])([F:17])[F:18])[CH2:11][CH:10]=2)=[C:29]([CH3:53])[CH:30]=1)=[O:36]

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 115653404,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)-1-cyclohexen-1-yl]-1,3,2-dioxaborolaneHCID 86692602HCID 86692602, compound

Product 1

HCID 86692601HCID 86692601, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)cyclohex-1-en-1-yl]-[1,3,2] dioxaborolane (163 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (37 mg), sodium carbonate (144 mg) and water (1.0 ml) were added at room temperature to a solution of N-(6-bromo-5-methylpyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (200 mg) described in Reference Example 189 in 1,4-dioxane (3.0 ml), and stirred at 100° C. under radiation of microwave for an hour. After completion of the reaction, water and ethyl acetate were added, filtered through Celite and the filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (146 mg) as a white solid.

Workup

  1. additionwere added
  2. filtrationfiltered through Celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-e6832daeedfa484f92c6b5aca0a0122d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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