2-(Trifluoromethyl)pyridine-5-boronic Acid → HCID 118195176, compound

HRID 923869Notes

Reaction equation

HRID 923869 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[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].[F:28][C:29]([F:40])([F:39])[C:30]1[N:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:33]3[CH:34]=[N:35][C:30]([C:29]([F:40])([F:39])[F:28])=[CH:31][CH:32]=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

Participants

3

Reactant 2

HCID 251342782-(Trifluoromethyl)pyridine-5-boronic AcidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195176HCID 118195176, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 54 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and (6-(trifluoromethyl)pyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.80 min, m/z=513.0 [M+H]+, m/z=511.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.80 (m, 1H) 1.79-1.91 (m, 1H) 2.85 (d, J=11.49 Hz, 1H) 3.16-3.27 (m, 2H) 3.40 (td, J=9.84, 7.21 Hz, 1H) 4.21 (br. s, 1H) 4.87 (br. s, 1H) 7.35 (d, J=8.31 Hz, 2H) 7.81-7.89 (m, 2H) 8.01 (d, J=7.58 Hz, 1H) 8.08-8.13 (m, J=8.31, 2.45, 2.45, 2.45 Hz, 2H) 8.80 (d, J=2.20 Hz, 1H) 8.85 (d, J=1.96 Hz, 1H) 10.18 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-35962f30501a4c47836e234799974835
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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