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

HRID 923941Notes

Reaction equation

HRID 923941 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].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1>>[OH:30][C:27]([CH:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][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 27343783-Pyridinylboronic acidHCID 899078115-Bromo-6-(3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181953822-(3-(2-Hydroxypropan-2-yl)pyrrolidin-1-yl)-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 pyridin-3-ylboronic acid to afford a white solid. HPLC (Condition 4) tR=4.68 min, UPLC-MS (Condition 7) m/z=487.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.87-1.10 (m, 6H) 1.53-1.80 (m, 2H) 1.96-2.12 (m, 1H) 3.00-3.20 (m, 3H) 3.24-3.33 (m, 1H) 4.25 (s, 1H) 7.32 (d, J=8.99 Hz, 2H) 7.46 (dd, J=7.82, 5.08 Hz, 1H) 7.74-7.89 (m, 3H) 8.00 (d, J=2.35 Hz, 1H) 8.55 (dd, J=4.69, 1.56 Hz, 1H) 8.61 (d, J=1.56 Hz, 1H) 8.74 (d, J=2.35 Hz, 1H) 10.14 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-87584d5ef2cb4107ab0105c2e65a04dd
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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