Cesium fluoride → HCID 22319639, compound

HRID 497627Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[F-].[Cs+].Cl[C:14]1[CH:22]=[C:21]2[C:17]([C:18]([NH:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35])=[N:19][N:20]2[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:16][CH:15]=1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([NH:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35])=[N:19][N:20]3[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:28])[CH3:29])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 102 °C

Procedure

840 mg of 4-fluorophenylboronic 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 heated at about 102° C. for 22 hours and is then allowed to return to room temperature. The reaction medium is taken up in 75 cm3 of ethyl acetate, filtered on a sinter funnel packed with Celite and then concentrated to dryness under reduced pressure (2 kPa; 50° C.). The work-up and the purification are performed by analogy with Example 41. 580 mg of N-[6-(4-fluorophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide are thus obtained in the form of a yellow oil.

Workup

customto return to room temperature
filtrationfiltered on a sinter funnel
concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
customThe work-up and the purification

Sources & evidence

ORD record: ord-aa01d8923e56467082a04c4d80c280a2
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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