Dimethylformamide → HCID 68279980, compound

HRID 68568Notes

Reaction equation

HRID 68568 reaction equation
Br[C:2]1[CH:3]=[C:4]([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)[S:5][C:6]=1[CH3:7].[CH3:25][N:26](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[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:4]3[S:5][C:6]([CH3:7])=[C:2]([C:25]#[N:26])[CH:3]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 867066483-(4-Bromo-5-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

Product 1

HCID 68279980HCID 68279980, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Tetrakis(triphenylphosphine)palladium(0) (1.2 g) is added to a solution of Zn(CN)2 (1.2 g) and 3-(4-bromo-5-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (4.6 g) in DMF (12 ml). After 1 h at 120° C. in the microwave, the reaction is quenched with water (150 ml) and ethyl acetate (100 ml) and filtered over celite. The aqueous phase is separated and further extracted two times with ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-thiophene-3-carbonitrile (2.2 g) as a beige crystal.

Workup

  1. customthe reaction is quenched with water (150 ml) and ethyl acetate (100 ml)
  2. filtrationfiltered over celite
  3. customThe aqueous phase is separated
  4. extractionfurther extracted two times with ethyl acetate
  5. washwashed with a saturated aqueous solution of NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-31eed939cc6e4d908813348718681268
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Reaction notes

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