(Pyrimidin-5-yl)boronic acid → [3-Methyl-6-pyrimidin-5-yl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517085Notes

Reaction equation

HRID 1517085 reaction equation
COC(=O)C1C(C)=CC(C2C=CC=C(C(F)(F)F)C=2)=NC=1OC.Cl[C:25]1[N:30]=[C:29]([C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[CH2:35][CH2:34]2)=[O:32])[C:28]([CH3:44])=[CH:27][C:26]=1[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=1.[N:55]1[CH:60]=[C:59](B(O)O)[CH:58]=[N:57][CH:56]=1>>[CH3:44][C:28]1[C:29]([C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[CH2:35][CH2:34]2)=[O:32])=[N:30][C:25]([C:59]2[CH:60]=[N:55][CH:56]=[N:57][CH:58]=2)=[C:26]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)[CH:27]=1

Participants

4

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 57441128HCID 57441128, compound

Product 1

HCID 57441151[3-Methyl-6-pyrimidin-5-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 5C, [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) was reacted with pyrimidine-5-yl-boronic acid to give the title compound as off-white amorphous solid. MS: 496.2 (MH+).

Sources & evidence

ORD record
ord-7ed44348c5aa4b2aa686670adc8324e0
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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