5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → N-(4-(Chlorodifluoromethoxy)phenyl)-5'-cyano-2-((2-hydroxyethyl)(methyl)amino)-[3,3'-bipyridine]-5-carboxamide

HRID 924031

Reaction equation

HRID 924031 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[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]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:35]2[CH:36]=[N:37][CH:38]=[C:39]([CH:42]=2)[C:40]#[N:41])O1>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([C:6]2[CH:21]=[C:2]([C:35]3[CH:36]=[N:37][CH:38]=[C:39]([C:40]#[N:41])[CH:42]=3)[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=2)=[O:8])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 899067025-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((2-hydroxyethyl)(methyl)amino)nicotinamide

Product 1

HCID 118195256N-(4-(Chlorodifluoromethoxy)phenyl)-5'-cyano-2-((2-hydroxyethyl)(methyl)amino)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((2-hydroxyethyl)(methyl)amino)nicotinamide (Stage 179.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow solid. UPLC-MS (Condition 3) tR=1.05 min, m/z=474.3 [M+H]+, m/z=472.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.70 (s, 3H) 3.48 (d, J=5.38 Hz, 2H) 3.56 (d, J=5.38 Hz, 2H) 4.66 (br. s, 1H) 7.36 (d, J=9.05 Hz, 2H) 7.81-7.93 (m, 2H) 8.15 (d, J=2.45 Hz, 1H) 8.46 (t, J=2.08 Hz, 1H) 8.77 (d, J=2.20 Hz, 1H) 9.01 (dd, J=7.21, 2.08 Hz, 2H) 10.23 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-a8bdebc6bebd4f6393b53e923fe5cd14
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Linked notes

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