(5-Fluoropyridin-3-yl)boronic acid → HCID 118195275, compound

HRID 923863Notes

Reaction equation

HRID 923863 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]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:15]=[CH:14][C:13]([O:16][C:17]([F:19])([F:18])[F:20])=[CH:12][CH:11]=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 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195275HCID 118195275, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 36 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and (5-fluoropyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.39 min, m/z=463.1 [M+H]+, m/z=461.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.79 (m, 1H) 1.79-1.91 (m, 1H) 2.88 (d, J=11.00 Hz, 1H) 3.17-3.27 (m, 2H) 3.36-3.45 (m, 1H) 4.21 (br. s, 1H) 4.87 (br. s, 1H) 7.35 (d, J=8.56 Hz, 2H) 7.79-7.90 (m, 3H) 8.08 (d, J=2.20 Hz, 1H) 8.51 (s, 1H) 8.60 (d, J=2.69 Hz, 1H) 8.78 (d, J=2.45 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-6868bacb9fe24e32a0b543a1f189ff83
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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