N,N-Dimethylglycine → 1-(4-(benzyloxy)-3-methylphenyl)-4-(trifluoromethyl)-1H-pyrazole

HRID 1520939Notes

Reaction equation

HRID 1520939 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:25])([F:24])[C:19]1[CH:20]=[N:21][NH:22][CH:23]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>N.C(OCC)(=O)C.[Cu](I)I.CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:21]2[CH:20]=[C:19]([C:18]([F:25])([F:24])[F:17])[CH:23]=[N:22]2)=[CH:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 673N,N-DimethylglycineHCID 11430Potassium CarbonateHCID 127777954-(Trifluoromethyl)-1H-pyrazoleHCID 589043791-(Benzyloxy)-4-iodo-2-methylbenzene

Product 1

HCID 681565621-(4-(benzyloxy)-3-methylphenyl)-4-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 222AmmoniaSolventHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(benzyloxy)-4-iodo-2-methylbenzene (850 mg, 2.6 mmol), 4-(trifluoromethyl)-1H-pyrazole (535 mg, 3.9 mmol), copper iodide (100 mg, 0.52 mmol), dimethylglycine (54 mg, 0.52 mmol), potassium carbonate (906 mg, 6.6 mmol), and DMSO (10 ml) was stirred at +120° for 20 hours. The reaction was cooled to the ambient temperature, diluted with 10 ml of 5% aqueous ammonia and 10 ml of ethyl acetate and vigorously stirred for 20 min. The mixture was extracted with ethyl acetate (2×20 ml). The combined organic extract was washed with brine, dried over anhydrous magnesium sulfate, and loaded on silica gel. Chromatography on a silica gel column, eluting with a gradient from 5% to 30% of ethyl acetate in heptane gave the target product as an oil, which crystallized upon standing to a colorless solid (670 mg, 77%). MS (M+1): 333.1.

Workup

  1. stirringvigorously stirred for 20 min
  2. extractionThe mixture was extracted with ethyl acetate (2×20 ml)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washChromatography on a silica gel column, eluting with a gradient from 5% to 30% of ethyl acetate in heptane

Sources & evidence

ORD record
ord-b161ed643dce424ba4382591525b8c9e
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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