3-Pyridinylboronic acid → HCID 118195228, compound

HRID 923846Notes

Reaction equation

HRID 923846 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][CH: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].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[OH:27][CH:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=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 27343783-Pyridinylboronic acidHCID 89904540HCID 89904540, compound

Product 1

HCID 118195228HCID 118195228, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 28 using 5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.1) and pyridin-3-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.78 min, m/z=445.0 [M+H]+, m/z=443.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.78 (m, 1H) 1.78-1.90 (m, 1H) 2.88 (d, J=11.25 Hz, 1H) 3.13-3.28 (m, 2H) 3.35-3.45 (m, 1H) 4.20 (br. s, 1H) 4.85 (d, J=3.42 Hz, 1H) 7.35 (d, J=8.80 Hz, 2H) 7.50 (dd, J=7.82, 4.89 Hz, 1H) 7.82 (d, J=8.07 Hz, 1H) 7.86 (d, J=9.05 Hz, 2H) 8.04 (d, J=2.20 Hz, 1H) 8.59 (dd, J=4.77, 1.34 Hz, 1H) 8.65 (d, J=1.96 Hz, 1H) 8.78 (d, J=2.20 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-3fe43bea0b1947798835b85a3ceaa2ef
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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