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

HRID 923942Notes

Reaction equation

HRID 923942 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][CH:24]([C:27]([OH:30])([CH3:29])[CH3:28])[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].[CH3:31][C:32]1[N:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[OH:30][C:27]([CH:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:35]3[CH:36]=[N:37][C:32]([CH3:31])=[CH:33][CH:34]=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)([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 899078115-Bromo-6-(3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181951012-(3-(2-Hydroxypropan-2-yl)pyrrolidin-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 113 using 5-bromo-6-(3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 113.1) and (6-methylpyridin-3-yl)boronic acid to afford an off-white amorphous solid. HPLC (Condition 4) tR=4.38 min, UPLC-MS (Condition 7) m/z=501.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.00 (d, J=16.03 Hz, 6H) 1.55-1.80 (m, 2H) 1.95-2.12 (m, 1H) 2.48 (s, 3H) 2.99-3.20 (m, 3H) 3.22-3.35 (m, 1H) 4.26 (s, 1H) 7.32 (dd, J=8.21, 5.86 Hz, 3H) 7.67 (dd, J=7.82, 2.35 Hz, 1H) 7.78-7.89 (m, 2H) 7.96 (d, J=2.35 Hz, 1H) 8.47 (d, J=2.35 Hz, 1H) 8.72 (d, J=2.35 Hz, 1H) 10.13 (s, 1H).

Workup

  1. customto afford an off-white amorphous solid

Sources & evidence

ORD record
ord-d1bab306229849e4b7c30c539954c0ca
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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