dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonate → dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)malonate

HRID 563436Notes

Reaction equation

HRID 563436 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]([CH:17]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67005843dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonateHCID 178418255HCID 178418255, compound

Product 1

HCID 59252807dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)malonateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonate (424 mg, 1.2 mmol) was dissolved in 10 mL dry THF and 1.0M phenylmagnesium bromide in THF (5 mL, 5.0 mmol) was added. The reaction mixture was stirred for 12 h. The reaction was quenched with MeOH then poured into brine and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on SiO2 by MPLC and eluting with 1:3 EtOAc/hexane. Obtained 435 mg (84% yield) of dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)malonate. MS found: (M+H)+=333.

Workup

  1. customThe reaction was quenched with MeOH
  2. additionthen poured into brine
  3. extractionextracted with EtOAc×3
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on SiO2 by MPLC
  8. washeluting with 1:3 EtOAc/hexane

Sources & evidence

ORD record
ord-f85b1c9818964def9cdd63e54c4a9a6c
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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