Sodium Carbonate → [5-(2-Chloro-5-trifluoromethyl-phenyl)-3-methyl-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517096Notes

Reaction equation

HRID 1517096 reaction equation
COC(C1C(C)=CC(C2C=CC=C(C(F)(F)F)C=2)=CN=1)=O.ClC1C=C([C:30]2[CH:31]=[C:32]([CH3:49])[C:33]([C:36]([N:38]3[CH2:43][CH2:42][CH:41]([N:44]4[CH2:48][CH2:47][CH2:46][CH2:45]4)[CH2:40][CH2:39]3)=[O:37])=[N:34][CH:35]=2)C=CC=1Cl.[Cl:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][C:52]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd](Cl)Cl>[Cl:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][C:52]=1[C:30]1[CH:31]=[C:32]([CH3:49])[C:33]([C:36]([N:38]2[CH2:39][CH2:40][CH:41]([N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[CH2:42][CH2:43]2)=[O:37])=[N:34][CH:35]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27826702-Chloro-5-(trifluoromethyl)phenylboronic acidHCID 574411233-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl esterHCID 58016731[5-(3,4-Dichloro-phenyl)-3-methyl-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 57441157[5-(2-Chloro-5-trifluoromethyl-phenyl)-3-methyl-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

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, (5-bromo-3-methyl-pyridin-2-yl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (see example 28) was reacted with 2-chloro-5-trifluoromethyl-phenyl-boronic acid, (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) and sodium carbonate in dioxane/water to give the title compound as light brown amorphous solid. MS: 452.2 (MH+, 1Cl).

Sources & evidence

ORD record
ord-4709aeef07fe42378751f12fd2f13152
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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