Hydrochloric Acid → 6-cyclopentyl-4H-isoquinoline-1,3-dione

HRID 2236452Notes

Reaction equation

HRID 2236452 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][Si](C(C)(C)C)(C)C)=[N:7][C:6]([O:20][Si](C(C)(C)C)(C)C)=[CH:5]2.[CH:28]1([Mg]Br)[CH2:32][CH2:31][CH2:30][CH2:29]1.CCOCC.Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1COCC1>[CH:28]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][C:6](=[O:20])[CH2:5]3)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 593000576-Bromo-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-isoquinolineHCID 178419650HCID 178419650, compound

Product 1

HCID 426258316-cyclopentyl-4H-isoquinoline-1,3-dione

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 6-bromo-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-isoquinoline (1.76 g, 3.75 mmole) is added tetrakis(triphenylphosphine)palladium (110 mg, 0.095 mmole) and 2M cyclopentyl magnesium bromide in ether (3.0 mL, 6.0 mmole). This mixture is heated using a microwave reactor at 75° C. for 600 sec. The mixture is cooled to room temperature, transferred to a flask with THF and water, then 2M hydrochloric acid (20 mL) is added and stirred for 4 hours at room temperature. The organic solvents were removed in vacuo, the mixture extracted with ethyl acetate, the organic layer dried over sodium sulfate filtered, evaporated and chromatographed with hexanes-ethyl acetate on silica gel to give a white solid, 268 mg (31%) MS (ESI): m/z 230.2 (M+H).

Workup

  1. temperatureThis mixture is heated
  2. customat 75° C.
  3. customfor 600 sec
  4. customThe organic solvents were removed in vacuo
  5. extractionthe mixture extracted with ethyl acetate
  6. dry with materialthe organic layer dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed with hexanes-ethyl acetate on silica gel
  10. customto give a white solid, 268 mg (31%)

Sources & evidence

ORD record
ord-ce4394cef63c46729cae2d156b479e39
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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