HCID 86687936, compound → HCID 86687937, compound

HRID 2401487Notes

Reaction equation

HRID 2401487 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([N+:16]([O-])=O)[C:3]=1[O:19][CH3:20].[H][H]>[Pd].C1COCC1.CN(C=O)C>[NH2:16][C:4]1[C:3]([O:19][CH3:20])=[CH:2][C:7]2[CH:8]=[C:9]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 86687936HCID 86687936, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86687937HCID 86687937, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

4-Chloro-5-methoxy-N,N-dimethyl-6-nitrobenzofuran-2-carboxamide (500 mg, 1.68 mmol), TEA (184 mg, 1.83 mmol) and 10% palladium on charcoal (90 mg) were stirred at room temperature in THF-DMF (2:1) (30 mL) under an atmosphere of hydrogen for 18 h. The reaction was recharged with hydrogen then allowed to stir for an additional 18 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford a brown solid (400 mg, quant.), which was taken through to the next step with no further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto afford a brown solid (400 mg, quant.), which
  4. customwas taken through to the next step with no further purification

Sources & evidence

ORD record
ord-f0b62329f6ee467ca8db5c6d4f8bf362
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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