3-Pyridinylboronic acid → (R)-4-(3-Hydroxypyrrolidin-1-yl)-3-(pyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 923833Notes

Reaction equation

HRID 923833 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].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=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:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 86702591(R)-3-bromo-4-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Product 1

HCID 118195245(R)-4-(3-Hydroxypyrrolidin-1-yl)-3-(pyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Procedure

The title compound was prepared in 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 pyridin-3-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.94 min, m/z=444.1 [M+H]+, m/z=442.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.68-1.79 (m, 1H) 1.85 (dt, J=8.62, 4.37 Hz, 1H) 2.66 (d, J=9.78 Hz, 1H) 2.98-3.07 (m, 2H) 3.16-3.25 (m, 1H) 4.18 (br. s, 1H) 4.84 (br. s, 1H) 6.95 (d, J=8.80 Hz, 1H) 7.33 (d, J=8.56 Hz, 2H) 7.50 (dd, J=7.82, 4.89 Hz, 1H) 7.80 (d, J=2.20 Hz, 1H) 7.81-7.89 (m, 3H) 7.92 (dd, J=8.68, 2.32 Hz, 1H) 8.56 (d, J=3.91 Hz, 1H) 8.65 (br. s, 1H) 10.10 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-737c3b193d4b4793bfc20e19e0db4658
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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