4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine → 4-(hydroxymethyl)-3-(2-morpholinopyridin-4-yl)-N-(3-(trifluoromethyl)phenyl)benzamide

HRID 594071Notes

Reaction equation

HRID 594071 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH2:21][OH:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:32]=2)O1>>[OH:22][CH2:21][C:20]1[CH:19]=[CH:18][C:4]([C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[O:6])=[CH:3][C:2]=1[C:31]1[CH:36]=[CH:35][N:34]=[C:33]([N:37]2[CH2:38][CH2:39][O:40][CH2:41][CH2:42]2)[CH:32]=1

Participants

3

Reactant 2

HCID 210816614-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholineHCID 904079633-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 862980914-(hydroxymethyl)-3-(2-morpholinopyridin-4-yl)-N-(3-(trifluoromethyl)phenyl)benzamideYield 91%

Procedure

The method used to prepare example X was followed using 3-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide and 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine to afford 4-(hydroxymethyl)-3-(2-morpholinopyridin-4-yl)-N-(3-(trifluoromethyl)phenyl)benzamide in a 91% yield. 1H NMR (400 MHz, <cd3od>) δ ppm 3.61-3.73 (m, 4H), 3.83-3.90 (m, 4H), 4.63 (s, 2H), 7.09-7.15 (m, 1H), 7.39-7.47 (m, 2H), 7.53-7.60 (m, 1H), 7.75-7.82 (m, 1H), 7.91-7.99 (m, 2H), 8.04-8.13 (m, 2H), 8.14-8.19 (m, 1H). LC/MS (m/z)=458.1 (MH+), Rt=0.73 min.

Workup

  1. customto prepare example X

Sources & evidence

ORD record
ord-7743901e97dc43ceb071e10ceb439a1d
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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