Sodium Carbonate → HCID 85972743, compound

HRID 2117337Notes

Reaction equation

HRID 2117337 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[C:10]3[CH:11]=[CH:12][N:13]=[CH:14][C:15]=3[CH:16]=[CH:17][CH:18]=2)=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl.O>O1CCOCC1>[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][C:34]([C:4]2[C:3]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:2][N:7]=[N:6][C:5]=2[NH:8][C:9]2[C:10]3[CH:11]=[CH:12][N:13]=[CH:14][C:15]=3[CH:16]=[CH:17][CH:18]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 22418719Chloroform waterHCID 87717666HCID 87717666, compound

Product 1

HCID 85972743HCID 85972743, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of Example 30 (0.08 g, 0.2 mmol) and 4-trifluoromethylphenylboronic acid (0.057 g, 0.3 mmol) in anhydrous dioxane (2 ml) was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (0.007 g, 0.009 mmol) and saturated aqueous sodium carbonate solution (0.3 ml). The mixture was irradiated in a microwave reactor at 170° C. for 10 minutes, allowed to cool to room temperature and poured onto a mixture of chloroform/water (30 ml/10 ml). The phases were separated and the aqueous phase was extracted two times more with chloroform. The combined organic layers were washed with brine, dried over sodium sulfate and adsorbed onto silica gel. Purification by flash column chromatography (ethyl acetate) yielded the title compound (35 mg, 34%) as a yellow solid. m/z (ES+) 511 (M+H+).

Workup

  1. customThe mixture was irradiated in a microwave reactor at 170° C. for 10 minutes
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted two times more with chloroform
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customPurification by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-18b80516004a4db1bcb6cb053a92b4af
Source dataset
uspto-grants-2008_10
Patent number
US07442701B2

Reaction notes

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