(5-Fluoropyridin-3-yl)boronic acid → HCID 118195333, compound

HRID 924041Notes

Reaction equation

HRID 924041 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]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1>>[F:28][C:29]1[CH:30]=[C:31]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)=[O:8])[CH:21]=2)[CH:32]=[N:33][CH:34]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86702604(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

Product 1

HCID 118195333HCID 118195333, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 186.1) and (5-fluoropyridin-3-yl)boronic acid to afford a yellow crystals. UPLC-MS (Condition 3) tR=1.08 min, m/z=479.4 [M+H]+, m/z=477.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.68-1.79 (m, 1H) 1.78-1.91 (m, 1H) 2.87 (d, J=11.29 Hz, 1H) 3.15-3.30 (m, 2H) 3.35-3.46 (m, 1H) 4.16-4.24 (m, 1H) 4.89 (d, J=3.39 Hz, 1H) 7.69 (d, J=8.66 Hz, 2H) 7.84 (dt, J=9.72, 2.16 Hz, 1H) 7.89-7.95 (m, 2H) 8.08 (d, J=2.38 Hz, 1H) 8.51 (s, 1H) 8.60 (d, J=2.64 Hz, 1H) 8.78 (d, J=2.26 Hz, 1H) 10.29 (s, 1H).

Workup

  1. customto afford a yellow crystals

Sources & evidence

ORD record
ord-8de76e38af8140f08240130dd1a46b2e
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…