HCID 21072277, compound → HCID 21072274, compound

HRID 1432157Notes

Reaction equation

HRID 1432157 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]1[CH2:9][CH2:8][CH:7]([CH3:22])[CH2:6][C:5]2=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]3[C:5]([C:4]=2[CH:3]=1)=[CH:6][C:7]([CH3:22])=[CH:8][CH:9]=3

Participants

3

Reactant 1

HCID 21072277HCID 21072277, compound

Product 1

HCID 21072274HCID 21072274, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 6-bromo-9-tert-butoxycarbonyl-3-methyl-1,2,3,4-tetrahydrocarbazole obtained in Example 24 (2.0 g, 5.49 mmol), 2,3-dichloro-4,5-dicyano-1,4-benzoquinone (2.62 g, 11.5 mmol) and activated 3 Å molecular sieves was added anhydrous benzene (17 mL) under a nitrogen atmosphere, and the mixture was refluxed for 20 h. The cooled reaction mixture was filtered and the filtrate evaporated. The crude product was chromatographed (PS with gradient elution up to PS:DCM 3:1) to afford 3-bromo-9-tert-butoxycarbonyl-6-methylcarbazole (1.64 g, 4.56 mmol, 83%) as a colourless solid. By-products were also obtained—6-bromo-9-tert-butoxycarbonyl-4-ethoxy-3-methylcarbazole (12 mg, 0.030 mmol, 0.5%) was obtained as a colourless oil, and 6-bromo-9-tert-butoxycarbonyl-1,2-dihydro-3-methylcarbazol-4-(3H)-one (52 mg, 0.144 mmol, 2.5%) was obtained as a pale yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customthe filtrate evaporated
  5. customThe crude product was chromatographed
  6. wash(PS with gradient elution up to PS:DCM 3:1)

Sources & evidence

ORD record
ord-15e6a2cbdcc2497386f543b3fa807207
Source dataset
uspto-grants-2009_11
Patent number
US07612036B2

Reaction notes

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