Potassium phosphate, dibasic, trihydrate → Ethyl 5-[2-(4-cyanophenyl)-2H-pyrazole-3-yl]-6-methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydropyridine-3-carboxylate

HRID 2089263Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].C([O-])(=O)C.[C:29]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[C:41](C3C=C(C(NCC[N+]4(C)CCCC4)=O)C(=O)N(C4C=CC=C(C(F)(F)F)C=4)C=3C)=[CH:40][CH:39]=[N:38]2)=[CH:33][CH:32]=1)#[N:30].O.O.O.P([O-])([O-])(O)=O.[K+].[K+].CC1(C)C(C)(C)OB(C2N(C3C=CC(C#N)=CC=3)N=CC=2)O1>CN(C=O)C.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[C:29]([C:31]1[CH:32]=[CH:33][C:34]([N:37]2[C:41]([C:2]3[CH:3]=[C:4]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5](=[O:19])[N:6]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=4)[C:7]=3[CH3:8])=[CH:40][CH:39]=[N:38]2)=[CH:35][CH:36]=1)#[N:30]

Participants

Conditions

Temperature: 55 °C

Procedure

Ethyl 5-iodo-6-methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydro-pyridine-3-carboxylate (synthesised according to WO2005/026123, Example 63 (b)) (9.02 g, 20 mmol), 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)benzonitrile (synthesised according to WO2009/061271, Example 1 intermediate) (8.85 g, 30.00 mmol), potassium hydrogenphosphate trihydrate (13.69 g, 60.00 mmol) and 1,1′-bis(di-tert-butylphosphino) ferrocene palladium dichloride (0.918 g, 1.40 mmol) were suspended in DMF (100 mL) in a 250 mL round-bottomed flask and the mixture was purged with argon. Then 1,1″-bis(di-tert-butylphosphino) ferrocene palladium dichloride (0.918 g, 1.40 mmol) was added and the reaction mixture was heated to 55° C. under vigorous stirring. After 30 and 90 min more 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)benzonitrile (1.4 g, 4.74 mmol and 2.5 g, 8.47 mmol) was added.

Workup

customthe mixture was purged with argon

Sources & evidence

ORD record: ord-1b376060b4774a7e9ef2c03708ef5311
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436024B2

Reaction notes

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