2-Methylpyridine-5-boronic acid → (R)-4-(3-Hydroxypyrrolidin-1-yl)-3-(6-methylpyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 923834Notes

Reaction equation

HRID 923834 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[CH3:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:21]2[CH:20]=[CH:19][C:4]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)=[O:6])=[CH:3][C:2]=2[C:32]2[CH:33]=[N:34][C:29]([CH3:28])=[CH:30][CH:31]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 86702591(R)-3-bromo-4-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Product 1

HCID 118195397(R)-4-(3-Hydroxypyrrolidin-1-yl)-3-(6-methylpyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 1 using (R)-3-bromo-4-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 2.1) and (6-methylpyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.92, m/z=458.1-459.1 [M+H]+, m/z=456.2-457.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.78 (m, 1H) 1.81-1.91 (m, 1H) 2.53 (s, 3H) 2.67 (d, J=10.27 Hz, 1H) 3.00-3.08 (m, 2H) 3.18-3.28 (m, 1H) 4.16-4.21 (m, 1H) 4.83 (d, J=3.42 Hz, 1H) 6.93 (d, J=9.05 Hz, 1H) 7.30-7.36 (m, 3H) 7.68 (dd, J=7.95, 2.32 Hz, 1H) 7.77 (d, J=2.20 Hz, 1H) 7.84-7.92 (m, 3H) 8.48 (d, J=1.96 Hz, 1H) 10.09 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-7666074b37c44680b4c6b8c6f7265a7f
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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