(E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate → methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoate

HRID 563403Notes

Reaction equation

HRID 563403 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](/[C:17](/[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59252822(E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate

Product 1

HCID 67005620methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoateYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate was dissolved in 30 mL EtOH in a Parr bottle and flushed with N2. 10% Pd on carbon was added and the reaction was put on a Parr shaker under 50 psi of H2 for 7 hours. LC-MS after this time indicated that the reaction was complete so the catalyst was filtered off and the solution concentrated in vacuo. The residue was purified using a 40 g MPLC column using a 10 to 25% EtOAc in hexanes gradient to give methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylpropanoate (1.1 g, 64%). MS found: (M+H)+=375.

Workup

  1. customflushed with N2
  2. addition10% Pd on carbon was added
  3. filtrationwas filtered off
  4. concentrationthe solution concentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-f5f0513510cc48e4b5f4aa43311333e7
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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