(5-Fluoropyridin-3-yl)boronic acid → HCID 118195255, compound

HRID 923914Notes

Reaction equation

HRID 923914 reaction equation
Br[C:2]1[N:21]=[C:20]([N:22]2[CH2:26][C@@H:25]([CH2:27][OH:28])[C@H:24]([OH:29])[CH2:23]2)[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)=[O:5].[F:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[N:35][CH:36]=1>>[F:30][C:31]1[CH:32]=[C:33]([C:19]2[C:20]([N:22]3[CH2:26][C@@H:25]([CH2:27][OH:28])[C@H:24]([OH:29])[CH2:23]3)=[N:21][CH:2]=[C:3]([C:4]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=3)=[O:5])[CH:18]=2)[CH:34]=[N:35][CH:36]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 89908098HCID 89908098, compound

Product 1

HCID 118195255HCID 118195255, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 86 using bromo-6-(trans-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 92.1) and (5-fluoropyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (Condition 3) tR=0.93 min, m/z=493.2 [M+H], m/z=491.4 [M−H]+, m/z=537.4 [M+ formic acid-H]; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.99-2.18 (m, 1H) 2.83-2.96 (m, 1H) 3.07-3.18 (m, 1H) 3.18-3.32 (m, 2H) 3.41-3.50 (m, 2H) 3.93-4.03 (m, 1H) 4.62-4.71 (m, 1H) 4.99 (d, J=4.27 Hz, 1H) 7.36 (d, J=9.03 Hz, 2H) 7.82-7.93 (m, 3H) 8.08 (d, J=2.38 Hz, 1H) 8.52 (d, J=1.63 Hz, 1H) 8.61 (d, J=2.63 Hz, 1H) 8.78 (d, J=2.38 Hz, 1H) 10.20 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-b75418fa76cd45c2adc45aef25002f25
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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