5-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole → [3-Methyl-6-(2-methyl-2H-pyrazol-3-yl)-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517117Notes

Reaction equation

HRID 1517117 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)COB([C:60]2[N:64]([CH3:65])[N:63]=[CH:62][CH:61]=2)OC1>>[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:60]2[N:64]([CH3:65])[N:63]=[CH:62][CH:61]=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

4

Reactant 3

HCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazoleHCID 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 ester

Product 1

HCID 58016717[3-Methyl-6-(2-methyl-2H-pyrazol-3-yl)-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

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 5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-1-methyl-1H-pyrazole to give the title compound as dark brown oil. MS: 498.2 (MH+).

Sources & evidence

ORD record
ord-15f26b0dc4e94786b0e499475d2ffaf0
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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