N,N-Dimethylglycine → HCID 69471830, compound

HRID 1063678Notes

Reaction equation

HRID 1063678 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH2:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:19][O:20][C:21](=[O:32])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][C:25]=1[CH3:31].C([O-])(=O)C.[Na+].CN(C)CC(O)=O>CN1CCCC1=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][O:20][C:21](=[O:32])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH:16]=[CH:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)=[CH:26][C:25]=1[CH3:31]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 517045Sodium AcetateHCID 20827035HCID 20827035, compoundHCID 22280101HCID 22280101, compound

Product 1

HCID 69471830HCID 69471830, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-trifluoromethyl-4′-vinyl-biphenyl (1.9 g, 7.7 mmol), (4-Bromo-2-methyl-phenoxy)-acetic acid methyl ester (2.0 g, 7.7 mmol), anhydrous sodium acetate (1.2 g, 14.6 mmol), N,N-dimethylglycine (0.23 g, 2.2 mmol), and palladium acetate (0.025 g, 0.11 mmol) in 10 ml of 1-methyl-pyrrolidin-2-one was heated at 130° C. for 10 h. The reaction mixture was partitioned between 250 ml of brine and 300 ml of ethyl acetate. The total mixture was filtered through a bed of Celite filter-aid. The organic layer was washed with 5% aqueous sodium carbonate solution (3×250 ml) and brine (2×250 ml), then dried over anhydrous sodium sulfate and concentrated. The residue was purified by normal phase chromatography to give {2-methyl-4-[2-(4′-trifluoromethyl-biphenyl-4-yl)-vinyl]-phenoxy}-acetic acid methyl ester; MS m/z 427 (M+1).

Workup

  1. customThe reaction mixture was partitioned between 250 ml of brine and 300 ml of ethyl acetate
  2. filtrationThe total mixture was filtered through a bed of Celite
  3. filtrationfilter-aid
  4. washThe organic layer was washed with 5% aqueous sodium carbonate solution (3×250 ml) and brine (2×250 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-819d001add0b45ff8ebab7ffb15ce39b
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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