Sodium Carbonate → HCID 178427387, compound

HRID 74448Notes

Reaction equation

HRID 74448 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23](I)[CH:22]=2)=[O:18].[C:39](=O)([O-])[O-:40].[Na+].[Na+].C([SiH](CC)CC)C.[C]=O>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([CH:39]=[O:40])[CH:22]=2)=[O:18]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 178418416HCID 178418416, compound2×HCID 178427388HCID 178427388, compound

Product 1

HCID 178427387HCID 178427387, compoundYield 92.8%

Reagents, catalysts & solvents 4

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

In a pressure-proof container, palladium acetate (1.0 mg, 0.0044 mmol), 1,3-bis(diphenylphosphino) propane (1.8 mg, 0.0044 mmol), [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[6-iodo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (100 mg, 0.16 mmol), and sodium carbonate (18 mg, 0.17 mmol) were dissolved in anhydrous N,N-dimethylformamide (DMF) (0.22 ml). After triethylsilane (52 μl, 0.33 mmol) was added, the air inside the container was replaced with carbon monoxide. Then, the reaction mixture was heated at 60° C. with stirring under pressure with carbon monoxide (3 atm) for 24 hours. After the reaction mixture was cooled to room temperature, the pressure was released to ambient pressure. The reaction mixture was diluted with ethyl acetate. The sodium carbonate was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/5) to give 2-[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazole-4-carbonyl]-1-(toluene-4-sulfonyl)-1H-indole-6-carbaldehyde as a yellow solid (80 mg, 85%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe sodium carbonate was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/5)

Sources & evidence

ORD record
ord-1f2ba203f0b44ca98da544a7be43d475
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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