Cesium fluoride → HCID 22319478, compound

HRID 497622Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[F-].[Cs+].Cl[C:15]1[CH:23]=[C:22]2[C:18]([C:19]([NH:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])=[N:20][N:21]2[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:17][CH:16]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([NH:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])=[N:20][N:21]3[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

0.81 g of 86% 4-methylthiophenylboronic 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 previously in Example 25, in 30 cm3 of dioxane. The mixture is then heated at about 100° C. for 20 hours, the temperature is allowed to return to room temperature over 72 hours and the reaction medium is then filtered on a sinter funnel and evaporated under reduced pressure (2 kPa; 50° C.). The work-up and the purification are performed by analogy with Example 41 above; 0.60 g of N-[6-(4-methylthiophenyl)-1-[[2-(trimethylsilyl)-ethoxy]methyl]-1H-indazol-3-yl]butanamide is thus obtained in the form of a yellow oil.

Workup

filtrationthe reaction medium is then filtered on a sinter funnel
customevaporated under reduced pressure (2 kPa; 50° C.)
customThe work-up and the purification

Sources & evidence

ORD record: ord-b1213a244d8a41dfa49e634a38bd3168
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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