2-Methylpyridine-5-boronic acid → (S)-6'-Methyl-2-(3-(methylamino)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923929Notes

Reaction equation

HRID 923929 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27](C)[C:28](=O)OC(C)(C)C)[CH2:23]2)=[N:4][CH:5]=[C:6]([C:8](=[O:21])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH:7]=1.[CH3:36][C:37]1[N:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1>>[CH3:36][C:37]1[N:42]=[CH:41][C:40]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@H:24]([NH:27][CH3:28])[CH2:23]3)=[N:4][CH:5]=[C:6]([C:8]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)=[O:21])[CH:7]=2)=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 118198937(5)-Tert-butyl (1-(3-bromo-5-((4-(trifluoromethoxy)phenyl)carbamoyl)pyridin-2-yl)pyrrolidin-3-yl)(methyl)carbamate

Product 1

HCID 118195215(S)-6'-Methyl-2-(3-(methylamino)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 93 using (S)-tert-butyl (1-(3-bromo-5-((4-(trifluoromethoxy)phenyl)carbamoyl)pyridin-2-yl)pyrrolidin-3-yl)(methyl)carbamate (Stage 102.1) and (6-methylpyridin-3-yl)boronic acid. LC-MS (Condition 6) tR=0.8 min, m/z=472.0 [M+H]+.

Sources & evidence

ORD record
ord-deb82d7633354d0baaa9357291ed9738
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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