(Pyridin-4-yl)boronic acid → HCID 118195172, compound

HRID 923848Notes

Reaction equation

HRID 923848 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][C:31](B(O)O)=[CH:30][CH:29]=1>>[OH:27][CH:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:31]3[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=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 2734379(Pyridin-4-yl)boronic acidHCID 89904540HCID 89904540, compound

Product 1

HCID 118195172HCID 118195172, 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 4-pyridineboronic acid to afford a yellow solid. UPLC-MS (condition 1) tR=1.62 min, m/z=445.0 [M+H]+, m/z=443.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.80 (m, 1H) 1.85 (dd, J=8.68, 4.28 Hz, 1H) 2.85 (d, J=11.49 Hz, 1H) 3.24 (dd, J=11.25, 4.16 Hz, 2H) 3.40-3.53 (m, 1H) 4.21 (br. s, 1H) 4.87 (br. s, 1H) 7.35 (d, J=8.80 Hz, 2H) 7.45 (d, J=5.87 Hz, 2H) 7.86 (d, J=9.29 Hz, 2H) 8.07 (d, J=2.45 Hz, 1H) 8.65 (d, J=5.14 Hz, 2H) 8.78 (d, J=2.20 Hz, 1H) 10.21 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-bf1b8c80437143e78117c99731f006ff
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…