Methanol → HCID 178497389, compound

HRID 38486Notes

Reaction equation

HRID 38486 reaction equation
C(N(CC)C(C)C)(C)C.C([N:13]1[C:21]2[C:16](=[CH:17][C:18](Br)=[CH:19][CH:20]=2)[C:15]([CH3:23])=[N:14]1)(=O)C.[CH3:24][OH:25].CN([CH:29]=[O:30])C>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].CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:23][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[C:18]([C:24]([O:30][CH3:29])=[O:25])[CH:17]=2)[NH:13][N:14]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 591273821-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

Product 1

HCID 178497389HCID 178497389, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

N,N-diisopropylethylamine (4.14 ml, 23.71 mmol) was added to a stirred mixture of 1-acetyl-5-bromo-3-methyl-1H-indazole (2.00 g, 7.90 mmol), DPPF (0.657 g, 1.185 mmol) and Pd(OAc)2 (0.266 g, 1.185 mmol) in DMF (20 ml)-MeOH (5 ml) at room temperature and the mixture was stirred in CO atomospher (1 atm) at 90° C. overnight. After the mixture was cooled and the CO gas was removed by N2 gas, the mixture was filtered through celite pad and the filtrate was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound as a pale brown solid.

Workup

  1. temperatureAfter the mixture was cooled
  2. customthe CO gas was removed by N2 gas
  3. filtrationthe mixture was filtered through celite pad
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silicagel column chromatography (hexane/EtOAc)
  6. customto give

Sources & evidence

ORD record
ord-f0e8b1f627094094a806186a6fa569ca
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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