Ethyl Acetate → HCID 58306985, compound

HRID 1909896Notes

Reaction equation

HRID 1909896 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][C:17]([C:26]([F:29])([F:28])[F:27])=[CH:18][C:19]=4[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=[CH:13]3)[CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(OCC)(=O)C>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][C:17]([C:26]([F:29])([F:27])[F:28])=[CH:18][C:19]=4[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=[CH:13]3)[CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 58307085HCID 58307085, compound

Product 1

HCID 58306985HCID 58306985, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

To a mixture of ethyl 1-(1,2,3,4-tetrahydroisoquinolin-7-ylmethyl)-5-(trifluoromethyl)-1H-indole-7-carboxylate (0.14 g) and ethyl acetate (10 mL) was added manganese dioxide (0.30 g) at room temperature. The reaction liquid was stirred for 6.5 hours under the condition for heating with reflux. In addition, to the reaction liquid were added toluene (10 mL) and manganese dioxide (0.30 g) at room temperature, followed by stirring at 110° C. for 1 day and then at 130° C. for 1 day. The reaction liquid was left to be cooled to room temperature, and filtered using Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25-30:70) to obtain ethyl 1-(isoquinolin-7-ylmethyl)-5-(trifluoromethyl)-1H-indole-7-carboxylate (85 mg).

Workup

  1. customThe reaction liquid
  2. temperaturefor heating
  3. temperaturewith reflux
  4. customIn addition, to the reaction liquid
  5. stirringby stirring at 110° C. for 1 day
  6. waitat 130° C. for 1 day
  7. customThe reaction liquid
  8. waitwas left
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25-30:70)

Sources & evidence

ORD record
ord-17f5d9000f234e3c9f1b9793771c7507
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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