2-Methylpyridine-5-boronic acid → 2-(3-(2-Hydroxypropan-2-yl)azetidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923978Notes

Reaction equation

HRID 923978 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:30][C:31]1[N:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1>>[OH:29][C:26]([CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:34]3[CH:35]=[N:36][C:31]([CH3:30])=[CH:32][CH:33]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1)([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 899072835-bromo-6-(3-(2-hydroxypropan-2-yl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181951572-(3-(2-Hydroxypropan-2-yl)azetidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-(2-hydroxypropan-2-yl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 142.1) and (6-methylpyridin-3-yl)boronic acid to afford an off-white foam. HPLC (Condition 4) tR=4.37 min, UPLC-MS (Condition 7) m/z=487.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 6H) 2.49 (s, 3H) 3.31 (br. s, 1H) 3.54-3.66 (m, 4H) 4.36 (d, J=0.78 Hz, 1H) 7.22-7.43 (m, 3H) 7.73 (dd, J=7.82, 2.35 Hz, 1H) 7.79-7.88 (m, 2H) 7.95 (d, J=2.35 Hz, 1H) 8.51 (d, J=1.96 Hz, 1H) 8.72 (d, J=2.35 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-ea5755da1e0c4f8e8bf68e06108de038
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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