Water → HCID 66855490, compound

HRID 2282228Notes

Reaction equation

HRID 2282228 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:24]([O:26][CH3:27])=[O:25])=[C:14](OS(C(F)(F)F)(=O)=O)[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC>[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1[C:14]1[N:15]=[C:11]([C:10]2[C:2]([CH3:1])=[N:3][N:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=23)[S:12][C:13]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 27343362,6-Difluorophenylboronic acidHCID 86649588HCID 86649588, compound

Product 1

HCID 66855490HCID 66855490, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of Methyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-thiazole-5-carboxylate (500 mg, 1.2 mmol) obtained in Example 13-B(ii), 2,6-difluorophenylboronic acid (375 mg, 2.4 mmol), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (97 mg, 0.12 mmol) and cesium carbonate (1.2 g, 3.6 mmol) in DME (20 mL), was added water (1 mL) and the mixture was stirred at 80° C. for 3 h. The reaction mixture was allowed to cool to room temperature, and then water (100 mL) was added. The aqueous mixture was extracted with EtOAc (100 mL×2) and the combined organic layer was dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc) to give the title compound (147 mg, 32%) as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous mixture was extracted with EtOAc (100 mL×2)
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-03caaf088de04a06bb0c8d4d278160d5
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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