5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → [6'-Amino-5-methyl-3-(3-trifluoromethyl-phenyl)-[2,3']bipyridinyl-6-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517105Notes

Reaction equation

HRID 1517105 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.CC1(C)C(C)(C)OB([C:63]2[CH:64]=[CH:65][C:66]([NH2:69])=[N:67][CH:68]=2)O1>>[NH2:69][C:66]1[N:67]=[CH:68][C:63]([C:25]2[C:26]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:52])([F:53])[F:54])[CH:46]=3)=[CH:27][C:28]([CH3:44])=[C:29]([C:31]([N:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)[CH2:35][CH2:34]3)=[O:32])[N:30]=2)=[CH:64][CH:65]=1

Participants

4

Reactant 3

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 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 58016719[6'-Amino-5-methyl-3-(3-trifluoromethyl-phenyl)-[2,3']bipyridinyl-6-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 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine to give the title compound as off-white solid. MS: 510.4 (MH+).

Sources & evidence

ORD record
ord-653a9343213346d2989345ded98c631c
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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