Triethylamine → 5-Bromo-2-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-4-methyl-pyridine

HRID 1027595Notes

Reaction equation

HRID 1027595 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:8]=[N:9][OH:10])=[N:6][CH:7]=1.ClN1C(=O)CCC1=O.[Cl:20][C:21]1[CH:26]=[C:25]([C:27]([C:29]([F:32])([F:31])[F:30])=[CH2:28])[CH:24]=[C:23]([Cl:33])[CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:8]2[CH2:28][C:27]([C:25]3[CH:24]=[C:23]([Cl:33])[CH:22]=[C:21]([Cl:20])[CH:26]=3)([C:29]([F:30])([F:32])[F:31])[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 1363413885-Bromo-4-methyl-pyridine-2-carbaldehyde oxime

Product 1

HCID 867159795-Bromo-2-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-4-methyl-pyridineYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of the compound obtained in Step C (2.2 g) in dimethylformamide (24 ml) was added N-chlorosuccinimide (1.4 g) in three portions at room temperature under argon. The reaction mixture was allowed to stir overnight at room temperature then a solution of 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (2.7 g, prepared as described in WO 2009/080250) in DMF (6 ml) was added followed by triethylamine (1.43 ml) in DMF (14 ml). The reaction stirred at room temperature for 1 hour then poured into ice water. A white solid precipitated, which was filtered, washed with water and dried under vacuum to give the title product (4.1 g). 1H-NMR (CDCl3, 400 MHz): 8.60 (s, 1H), 7.90 (s, 1H), 7.50 (s, 2H), 7.40 (s, 1H), 4.20 (d, 1H), 3.85 (d, 1H), 2.45 (s, 3H),

Workup

  1. stirringThe reaction stirred at room temperature for 1 hour
  2. customA white solid precipitated
  3. filtrationwhich was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c83d5747283048f3918e4e41d73cb705
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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