HCID 21072277, compound → HCID 21072274, compound

HRID 1373002Notes

Reaction equation

HRID 1373002 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, 0.14 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-a0ebcee1a2e3449c9bf0b6e44f5042a8
Source dataset
uspto-grants-2007_01
Patent number
US07160854B2

Reaction notes

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