Dimethylformamide → HCID 23020240, compound

HRID 917353Notes

Reaction equation

HRID 917353 reaction equation
CN(C)C=O.[F:6][C:7]([F:19])=[C:8]([CH3:18])[CH2:9][CH2:10][CH2:11][CH2:12]CS([O-])(=O)=O.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29]([OH:31])=[O:30].C(=O)([O-])O.[Na+]>O>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29]([O:31][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([CH3:18])=[C:7]([F:6])[F:19])=[O:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72899Indole-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 86595303HCID 86595303, compound

Product 1

HCID 23020240HCID 23020240, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 20 ml of N,N-dimethylformamide were dissolved 1.50 g (6.6 mmol) of 6,6-difluoro-5-methyl-5-hexenylmethanesulfonate and 1.30 g (8.1 mmol) of 1H-indole-2-carboxylicacid, followed by the addition of 1.40 g (17 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 1.70 g (yield: 88%) of 6,6-difluoro-5-methyl-5-hexenyl 1H-indole-2-carboxylate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-a43b1907463643308e57426e50a78d6c
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

Loading…