Cesium fluoride → HCID 22319497, compound

HRID 497629Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[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>[CH3:2][C:1]([C:5]1[CH:10]=[CH:9][C:8]([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:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 102 °C

Procedure

840 mg of 4-tert-butylphenylboronic 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 heated at about 102° C. for 21 hours and 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. 1.13 g of N-[6-[4-(1,1-dimethylethyl)phenyl]-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 through a sinter funnel
concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
customThe work-up and the purification

Sources & evidence

ORD record: ord-73b3422ee718475caf661c1d2652aeff
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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