Potassium Carbonate → HCID 68350592, compound

HRID 508204Notes

Reaction equation

HRID 508204 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:23])=[O:12])[N:3]=1.[C:24]([O-:27])([O-])=[O:25].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([F:22])([F:21])[F:20])[C:13]=1[C:11]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:24](=[O:25])[O:27][CH2:2]3)=[N:3]1)=[O:12]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 68279205HCID 68279205, compound

Product 1

HCID 68350592HCID 68350592, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(0.97 g, 2.48 mmol), (3-bromo-1H-indazol-1-yl)(2-chloro-6-(trifluoro methyl)phenyl)methanone (1.0 g, 2.48 mmol), K2CO3 (1.03 g, 7.44 mmol) and Pd(PPh3)4 (0.143 g, 0.12 mmol) were suspended in 1,4-dioxane (15 mL) and H2O (3 mL). The reaction mixture was heated at 100° C. in a microwave reactor for 2 h. The reaction mixture was cooled to rt and diluted with H2O. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (PE:EA=4:1) to afford the title compound as a pale yellow oil. LCMS (ESI) calc'd for C23H13ClF3N2O3 [M+H]+: 457. found: 457.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (PE:EA=4:1)

Sources & evidence

ORD record
ord-b32cfd92338740f69c71778beb3ab80b
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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