2-Furancarbonyl chloride → HCID 14032527, compound

HRID 845619Notes

Reaction equation

HRID 845619 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([Cl:24])=[O:23]>C(Cl)(Cl)Cl>[ClH:24].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[N:9]1)=[O:23]

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 178480237HCID 178480237, compound

Product 1

HCID 14032527HCID 14032527, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole, 2.7 ml of 2-furoyl chloride (95% pure) and 60 ml of chloroform was refluxed for 3 hrs. The mixture was filtered. The filtrate was evaporated under reduced pressure, the residue was triturated with ethyl acetate and the solid was collected. The solid and filtrate were combined and recrystallized twice from ethanol to yield 3.3 g (51.5%) of product, mp 268°-270° C.

Workup

  1. temperaturewas refluxed for 3 hrs
  2. filtrationThe mixture was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was triturated with ethyl acetate
  5. customthe solid was collected
  6. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-adf842ea3db24d3aab581083fd1ee688
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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