Dimethylformamide → HCID 25144318, compound

HRID 1470396Notes

Reaction equation

HRID 1470396 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][NH2:33].CN([CH:37]=[O:38])C>>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:37]([NH:33][CH2:32][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=4)=[O:38])=[C:3]([CH3:25])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 195092-PyridinemethanamineHCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 25144318HCID 25144318, compoundYield 34%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (1.02 g, 2.24 mmol), 2-picolylamine (369 mg, 3.41 mmol), Pd(dppf)C12 (92 mg, 0.13 mmol) triethylamine (5.2 mL, 3.8 g. 37 mmol) and DMF (50 mL) was flushed with carbon monoxide and stirred under an atmosphere of CO at 100° C. for 26 h. The solvent was removed in vacuum and the residue was taken up in EtOAc, filtered and evaporated. The residue was chromatographed on SiO2 to give the title compound (391 mg, 34%).

Workup

  1. customwas flushed with carbon monoxide
  2. customThe solvent was removed in vacuum
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-57b98383b531439d83fdd95001386016
Source dataset
uspto-grants-2015_04
Patent number
US09006447B2

Reaction notes

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