(Pyrimidin-5-yl)boronic acid → 5-(Pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 629075Notes

Reaction equation

HRID 629075 reaction equation
Br[C:2]1[CH:3]=[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].[N:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[N:24][CH:23]=1>>[N:22]1[CH:27]=[C:26]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:21]=2)[C:7]([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)=[O:8])[CH:25]=[N:24][CH:23]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 46840185-bromo-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 722032845-(Pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 1 using 5-bromo-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 42.1) and pyrimidin-5-ylboronic acid to afford an off-white solid. UPLC-MS (Condition 1) tR=2.09 min, m/z=361.0 [M+H]+, m/z=359.0 [M−H]−; 1H-NMR: (400 MHz, DMSO-d6) δ ppm: 7.41 (d, J=8.56 Hz, 1H) 7.90 (d, 1H) 8.72 (t, J=2.20 Hz, 1H) 9.16 (dd, 1H) 9.23 (dd, 1H) 9.29 (s, 1H) 9.32 (s, 2H) 10.67 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-abeb81af009941d79c4714e5798314a8
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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