Sodium Carbonate → HCID 178422650, compound

HRID 1517113Notes

Reaction equation

HRID 1517113 reaction equation
COC(C1C(C)=CC(C2C=CC=C(C(F)(F)F)C=2)=CN=1)=O.Cl[C:23]1[N:28]=[C:27]([C:29]([N:31]2[CH2:36][CH2:35][CH:34]([N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]2)=[O:30])[C:26]([CH3:42])=[CH:25][C:24]=1[C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:52])([F:51])[F:50])[CH:44]=1.CC1(C)C(C)(C)OB([C:61]2[CH:65]=[CH:64][NH:63][N:62]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd](Cl)Cl>[CH3:42][C:26]1[C:27]([C:29]([N:31]2[CH2:36][CH2:35][CH:34]([N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]2)=[O:30])=[N:28][C:23]([C:61]2[CH:65]=[CH:64][NH:63][N:62]=2)=[C:24]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:52])([F:51])[F:50])[CH:44]=2)[CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 574411233-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl esterHCID 178431094HCID 178431094, compound

Product 1

HCID 178422650HCID 178422650, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to the procedure described for the preparation of intermediate 1A, [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) was reacted with 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole, (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) and sodium carbonate in dioxane/water at 120° C. to give the title compound as colorless solid. MS: 484.2 (MH+)

Sources & evidence

ORD record
ord-b8c63d414f9f43b0831838b5da294127
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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