Ethanol → HCID 58138783, compound

HRID 2382967Notes

Reaction equation

HRID 2382967 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21](Br)[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N([CH2:38][CH3:39])CC)C.[CH2:40]([OH:42])C.[C]=[O:44]>O.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[CH2:38]([O:44][C:40]([C:21]1[CH:20]=[C:19]2[C:15]([CH:16]=[N:17][N:18]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:14]([C:12](=[O:13])[NH:11][CH2:10][C:9]2[CH:31]=[CH:32][C:6]([S:3](=[O:5])(=[O:4])[NH:2][CH3:1])=[CH:7][CH:8]=2)[CH:22]=1)=[O:42])[CH3:39]

Participants

8

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamideHCID 178418416HCID 178418416, compound

Product 1

HCID 58138783HCID 58138783, compound

Reagents, catalysts & solvents 3

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide (0.2 g, 0.4 mmol), triethylamine (0.1 g, 0.9 mmol), dichlorobis(benzonitrile)palladium (0.02 g, 0.05 mmol) and 1,1-bis(diphenylphosphino)ferrocene (0.03 g, 0.05 mmol) was charged in a sealed tube with absolute ethanol (15 mL). The solution was placed under 15 bars of carbon monoxide and warmed at 140° C. for 4 hours. The mixture was cooled to room temperature and returned to atmospheric pressure. The reaction was diluted with water (30 mL) and the solid was collected by filtration. The filtrate was diluted with water (20 mL) and ethyl acetate (20 mL). The organic layer was separated and washed with brine (10 mL) and dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 30-70% ethyl acetate in hexanes to afford the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe solid was collected by filtration
  3. additionThe filtrate was diluted with water (20 mL) and ethyl acetate (20 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 30-70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f2a496d9614c4d6d8c71405a24487318
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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