Ethyl Acetate → 3-[2-methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-propionic acid ethyl ester

HRID 915489Notes

Reaction equation

HRID 915489 reaction equation
I[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:4]=1.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20].C([N-]C(C)C)(C)C.[Li+]>CN1C(=O)N(C)CCC1>[CH2:23]([O:22][C:19](=[O:21])[CH2:20][CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:4]=1)[CH3:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 692828125-iodomethyl-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazole

Product 1

HCID 692824853-[2-methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

In analogy to the procedure described in example 20 b], 5-iodomethyl-1-methyl-3-(4-trifluoromethyl-phenyl)-1H-pyrazole was reacted with ethyl acetate in the presence of lithium diisopropylamide and DMPU to obtain 3-[2-methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-propionic acid ethyl ester as yellow solid.

Sources & evidence

ORD record
ord-5ecf6487ed1d4debb57867afacb91247
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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