5-Bromo-2-furanecarboxylic acid → 5-Chloro-3-(5-bromo-2-furanoyl)-2-oxindole-1-carboxamide

HRID 1463502Notes

Reaction equation

HRID 1463502 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]([NH2:22])=[O:21])[C:15](=[O:23])[CH2:14]2.BrC1OC(C(Cl)=O)=CC=1>S(Cl)(Cl)=O.CN(C1C=CN=CC=1)C.CN(C)C=O>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]([NH2:22])=[O:21])[C:15](=[O:23])[CH:14]2[C:7]([C:5]1[O:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9]

Participants

7

Reactant 3

HCID 685115-Bromo-2-furanecarboxylic acidHCID 27570115-Bromofuran-2-carbonyl chlorideHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide

Product 1

HCID 867450435-Chloro-3-(5-bromo-2-furanoyl)-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

Using the procedure of Example 32, 1.91 g (10.0 mmoless) of commercially available 5-bromo-2-furancarboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HC1. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 1 hour
  3. customthe acid chloride product was recovered
  4. customAfter a reaction time of about 45 minutes
  5. additionby pouring into 250 ml of 1N HC1
  6. customThe product was recrystallized from acetic acid
  7. washwashed with acetic acid
  8. dry with materialhexane and dried overnight in vacuo at room temperature
  9. customThe resulting product then was dried
  10. temperatureover refluxing isopropanol under high vacuum

Sources & evidence

ORD record
ord-2b727cb035564b1aa71a01df88a6a503
Source dataset
uspto-grants-1994_04
Patent number
US05300655

Reaction notes

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