3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 2-(Ethyl(2-hydroxyethyl)amino)-5'-fluoro-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 924053Notes

Reaction equation

HRID 924053 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]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[CH2:26]([N:22]([CH2:23][CH2:24][OH:25])[C:3]1[C:2]([C:33]2[CH:32]=[N:31][CH:30]=[C:29]([F:28])[CH:34]=2)=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1)[CH3:27]

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 89906420HCID 89906420, compound

Product 1

HCID 1181952982-(Ethyl(2-hydroxyethyl)amino)-5'-fluoro-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using 5-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 195.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford an off-white foam. HPLC (Condition 4) tR=5.89 min, UPLC-MS (Condition 3) tR=1.15 min, m/z=481.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.89 (t, J=7.04 Hz, 3H) 3.15 (m, J=6.60 Hz, 2H) 3.32-3.41 (m, 2H) 3.47 (m, J=5.90 Hz, 2H) 4.61 (t, J=1.00 Hz, 1H) 7.68 (d, J=8.60 Hz, 2H) 7.86-8.00 (m, 3H) 8.07 (d, J=2.35 Hz, 1H) 8.54-8.67 (m, 2H) 8.75 (d, J=2.35 Hz, 1H) 10.34 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-cdd3978e28ef4e8f9ce6fbfff4ee0dae
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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