Methanol → Methyl 3-methyl-1-phenyl-1H-indazole-5-carboxylate

HRID 1097007Notes

Reaction equation

HRID 1097007 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[N:6]=[C:5]2[CH3:17].C(N(C(C)C)CC)(C)C.[CH3:27][OH:28].CN([CH:32]=[O:33])C>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:17][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:27]([O:33][CH3:32])=[O:28])[CH:3]=2)[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 579310235-Bromo-3-methyl-1-phenyl-1H-indazole

Product 1

HCID 57930953Methyl 3-methyl-1-phenyl-1H-indazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
70 °C

Procedure

The mixture of 5-bromo-3-methyl-1-phenyl-1H-indazole (642 mg), Pd(OAc)2 (52 mg), DPPF (123 mg), diisopropyl ethyl amine (1.14 ml) in DMF (5 ml)-MeOH (5 ml) was purged with CO and stirred at 70° C. under CO atmosphere for over night. The cooled reaction mixture was evaporated and the residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound as brown oil.

Workup

  1. customwas purged with CO
  2. customThe cooled reaction mixture
  3. customwas evaporated
  4. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-f517e58464ca4770b41a32a5017a270a
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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