tert-butyl 2-(benzyloxy)-7-(N-methylformamido)-9H-carbazole-9-carboxylate → tert-butyl 2-hydroxy-7-(N-methylformamido)-9H-carbazole-9-carboxylate

HRID 1879542Notes

Reaction equation

HRID 1879542 reaction equation
C([O:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([N:22]([CH3:25])[CH:23]=[O:24])=[CH:16][CH:17]=3)[N:12]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:11]=2[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([N:22]([CH3:25])[CH:23]=[O:24])=[CH:16][CH:17]=3)[N:12]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:11]=2[CH:10]=1

Participants

4

Reactant 1

HCID 86651372tert-butyl 2-(benzyloxy)-7-(N-methylformamido)-9H-carbazole-9-carboxylate

Product 1

HCID 58225214tert-butyl 2-hydroxy-7-(N-methylformamido)-9H-carbazole-9-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To tert-butyl 2-(benzyloxy)-7-(N-methylformamido)-9H-carbazole-9-carboxylate (120 mg, 0.28 mmol) in 50 mL MeOH was added Palladium on activated carbon (50 mg). The mixture was stirred at rt under H2 atmosphere for 3 h. Solid was filtered off and the filtrate was concentrated to afford tert-butyl 2-hydroxy-7-(N-methylformamido)-9H-carbazole-9-carboxylate as a brown solid (95 mg, 100%). This material was used directly for the next reaction without purification. MS (ESI) m/z 341 (M+H+).

Workup

  1. filtrationSolid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-93e446314c084cb887cd597dec77964b
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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