3-Fluorophthalic anhydride → 2-(4-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]methyl}-2-methylphenyl)-4-fluoro-1H-isoindole-1,3(2H)-dione

HRID 2243246Notes

Reaction equation

HRID 2243246 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:31]=[CH:32][C:33]=1[NH2:34])[CH2:17][N:18]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][C:20]([C:27]([F:30])([F:29])[F:28])=[N:19]1>C(O)(=O)C>[F:30][C:27]([F:28])([F:29])[C:20]1[CH:21]=[C:22]([C:23]([F:26])([F:24])[F:25])[N:18]([CH2:17][C:16]2[CH:31]=[CH:32][C:33]([N:34]3[C:8](=[O:9])[C:3]4[C:4](=[CH:10][CH:11]=[CH:12][C:2]=4[F:1])[C:5]3=[O:7])=[C:14]([CH3:13])[CH:15]=2)[N:19]=1

Participants

4

Reactant 2

HCID 695513-Fluorophthalic anhydrideHCID 592103951-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole

Product 1

HCID 592103852-(4-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]methyl}-2-methylphenyl)-4-fluoro-1H-isoindole-1,3(2H)-dioneYield 76.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Fluorophthalic anhydride (4.98 g) and 1-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (9.70 g) were refluxed in acetic acid (43 ml) for 3 hours. After finishing the reaction, the acetic acid was distilled off under the reduced pressure and the obtained crude crystals were washed with t-butyl methyl ether to obtain the aimed 2-{4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl-methyl]-2-methylphenyl}-4-fluoroisoindol-1,3-dione (10.80 g). mp. 158-159° C.

Workup

  1. customthe reaction
  2. distillationthe acetic acid was distilled off under the reduced pressure
  3. customthe obtained crude crystals
  4. washwere washed with t-butyl methyl ether

Sources & evidence

ORD record
ord-272c9026925a4dd992e7dc7dd2a31fa3
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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