Cesium fluoride → HCID 22319635, compound

HRID 497633Notes

Reaction equation

[CH3:1][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>[CH3:1][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: 104 °C

Procedure

555 mg of 4-methylphenylboronic 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 104° C. for 5 hours 30 minutes and the temperature is then allowed to return to room temperature over 16 hours. The reaction medium is diluted with 75 cm3 of ethyl acetate and filtered through a sinter funnel packed with Celite, and the filtrate is concentrated to dryness under reduced pressure (2 kPa; 50° C.). The work-up and the purification are performed by analogy with Example 41. 1.1 g of N-[6-(4-methylphenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide are obtained in the form of a yellow oil.

Workup

filtrationfiltered through a sinter funnel
concentrationthe filtrate is concentrated to dryness under reduced pressure (2 kPa; 50° C.)
customThe work-up and the purification

Sources & evidence

ORD record: ord-7ed822db0acb4111860b8be6583445fd
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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