Cesium fluoride → HCID 22319562, compound

HRID 497632Notes

Reaction equation

HRID 497632 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[F-].[Cs+].Cl[C:17]1[CH:25]=[C:24]2[C:20]([C:21]([NH:34][C:35](=[O:39])[CH2:36][CH2:37][CH3:38])=[N:22][N:23]2[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=[CH:19][CH:18]=1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]([NH:34][C:35](=[O:39])[CH2:36][CH2:37][CH3:38])=[N:22][N:23]3[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:31])[CH3:32])=[CH:19][CH:18]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 10406687N-[6-chloro-1-[[2-(trimethylsilyl)ethoxy)methyl]-1H-indazol-3-yl)butanamide

Product 1

HCID 22319562HCID 22319562, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

775 mg of 4-trifluoromethylphenylboronic acid, 1.24 g of caesium fluoride, 13.5 mg of palladium acetate and finally 31 mg of 2-dicyclohexylphosphine-2-(N,N-dimethylamino)biphenyl are added to 1 g of N-[6-chloro-1-[[2-(trimethylsilyl)-ethoxy]methyl]-1H-indazol-3-yl]butanamide, described in Example 25, in 30 cm3 of dioxane. The mixture is then refluxed for 18 hours, the temperature is then allowed to return to room temperature and the reaction medium is diluted with 75 cm3 of ethyl acetate, filtered through a sinter funnel packed with Celite and concentrated to dryness under reduced pressure (2 kPa; 50° C.). The work-up and the purification are performed by analogy with Example 41. 1 g of N-[6-[4-(trifluoromethyl)phenyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide is thus obtained in the form of a yellow oil in a purity of 95%.

Workup

  1. temperatureThe mixture is then refluxed for 18 hours
  2. customto return to room temperature
  3. filtrationfiltered through a sinter funnel
  4. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  5. customThe work-up and the purification

Sources & evidence

ORD record
ord-74553c4e046447cbbf987ac73194f0d3
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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