1,2-Dichloroethane → N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)isonicotinamide

HRID 594024

Reaction equation

HRID 594024 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27]C=1)[C:23](O)=[O:24].C1C=[N:35]C2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][N:35]=[C:20]([C:19]([F:30])([F:29])[F:18])[CH:21]=2)=[CH:4][C:3]=1[B:9]1[O:10][C:11]([CH3:17])([CH3:16])[C:12]([CH3:15])([CH3:14])[O:13]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 99633-(Trifluoromethyl)benzoic acidHCID 181649HOAtHCID 160860894-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 90408534N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)isonicotinamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.) and 3-(trifluoromethyl)benzoic acid (1.1 equiv.) in DMF (0.27 M) was added HOAt (1.3 equiv.) and EDC (1.3 equiv.) After 3 h the reaction mixture was diluted with water and then extracted with EtOAc. The organic phase was washed sequentially with 1 M aqueous sodium hydroxide and brine and was then dried over sodium sulfate. The solution was concentrated and dried under vacuo to give N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)isonicotinamide in 91% yield. LCMS (m/z) (M+H)=407.1, Rt=1.13 min.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed sequentially with 1 M aqueous sodium hydroxide and brine
  3. dry with materialwas then dried over sodium sulfate
  4. concentrationThe solution was concentrated
  5. customdried under vacuo

Sources & evidence

ORD record
ord-009e13668b99438fbb81b0af0d1aed39
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Linked notes

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