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

HRID 924049Notes

Reaction equation

HRID 924049 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]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:33]=1>>[F:27][C:28]1[CH:33]=[C:32]([C:2]2[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)[CH:31]=[N:30][CH:29]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 89906571HCID 89906571, compound

Product 1

HCID 1181952235'-Fluoro-2-((2-hydroxyethyl)(methyl)amino)-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-((2-hydroxyethyl)(methyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 192.1) 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=5.7 min, UPLC-MS (Condition 3) tR=1.10 min, m/z=467.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.69 (s, 3H) 3.41-3.63 (m, 4H) 4.66 (t, J=5.28 Hz, 1H) 7.68 (d, J=8.99 Hz, 2H) 7.82-7.97 (m, 3H) 8.11 (d, J=2.35 Hz, 1H) 8.49-8.63 (m, 2H) 8.74 (d, J=2.35 Hz, 1H) 10.31 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-6deb7b9e44254f699900e09072b84111
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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