Cesium carbonate → HCID 86692545, compound

HRID 1748592Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[C:15]=2[CH3:16])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:33]([O:37][C:38]([N:40]1[CH2:45][CH:44]=[C:43](B2OC(C)(C)C(C)(C)O2)[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].O1CCOCC1>O>[C:33]([O:37][C:38]([N:40]1[CH2:41][CH:42]=[C:43]([C:2]2[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]3[CH:12]=[N:13][N:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=4)[C:15]=3[CH3:16])=[O:10])=[CH:4][CH:3]=2)[CH2:44][CH2:45]1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 110 °C

Procedure

To N-(6-bromopyridin-3-yl)-5-methyl-1-[5-(tri fluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (3.0 g), cesium carbonate (6.4 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloridedichloromethane complex (287 mg), and N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (2.28 g) were added 1,4-dioxane (26 ml) and water (7 ml), and stirred at 110° C. for 6.5 hours. To the reaction solution was added water, and the obtained solid was washed with a mixed solution of n-hexane and ethyl acetate to give N-[6-(1-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (3.53 g) as a brown solid.

Workup

washthe obtained solid was washed with a mixed solution of n-hexane and ethyl acetate

Sources & evidence

ORD record: ord-81126a5beb404743b6809da65f332baf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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