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

HRID 924035Notes

Reaction equation

HRID 924035 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[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:36]2[CH:37]=[N:38][CH:39]=[C:40]([CH:43]=2)[C:41]#[N:42])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:36]3[CH:37]=[N:38][CH:39]=[C:40]([C:41]#[N:42])[CH:43]=3)[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[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 899068415-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide

Product 1

HCID 118195139N-(4-(Chlorodifluoromethoxy)phenyl)-5'-cyano-2-(ethyl(2-hydroxyethyl)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-(ethyl(2-hydroxyethyl)amino)nicotinamide (Stage 182.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow solid. UPLC-MS (Condition 3) tR=1.10 min, m/z=486.3 [M+H]+, m/z=488.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.90 (t, J=6.97 Hz, 3H) 3.15 (q, J=7.09 Hz, 2H) 3.37 (t, J=5.99 Hz, 2H) 3.44-3.55 (m, 2H) 4.62 (br. s, 1H) 7.36 (d, J=9.29 Hz, 2H) 7.82-7.90 (m, 2H) 8.11 (d, J=2.45 Hz, 1H) 8.54 (t, J=2.08 Hz, 1H) 8.79 (d, J=2.45 Hz, 1H) 9.04 (dd, J=5.62, 1.96 Hz, 2H) 10.26 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-a6bb159ec12c4962978baecbd07922ea
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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