Triacetoxyperiodinane → HCID 86642954, compound

HRID 661944Notes

Reaction equation

HRID 661944 reaction equation
[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH2:15][OH:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:17]([NH2:19])=[O:18])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]=[O:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:17]([NH2:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66606607HCID 66606607, compound

Product 1

HCID 86642954HCID 86642954, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step 1 A partial solution of 4-bromo-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (Example 30-2, 1.00 g, 3.13 mmol) in THF (75 mL) was stirred at rt and treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane, 1.993 g, 4.70 mmol). After 45 min, the solution was diluted with EtOAc and washed with 5% aqueous sodium sulfite, NaHCO3 (aq), and brine, then was dried and concentrated. The residue was triturated with methanol, and the precipitate was collected by filtration, washed with methanol and dried to provide 4-bromo-7-formyl-9H-carbazole-1-carboxamide as a tan powder (ca. 85% purity, 948 mg, 81%) used without purification. 1H NMR (400 MHz, DMSO-d6) δ 12.13 (1H, s), 10.14 (1H, s), 8.80 (1H, d, J=8.1 Hz), 8.38 (1H, d, J=0.9 Hz), 8.28 (1H, br. s.), 7.97 (1H, d, J=8.1 Hz), 7.83 (1H, dd, J=8.3, 1.4 Hz), 7.64 (1H, br. s.), 7.54 (1H, d, J=8.1 Hz). Mass spectrum m/z 317, 319 (M+H)+.

Workup

  1. washwashed with 5% aqueous sodium sulfite, NaHCO3 (aq), and brine
  2. customwas dried
  3. concentrationconcentrated
  4. customThe residue was triturated with methanol
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with methanol
  7. customdried

Sources & evidence

ORD record
ord-f2cfeaee12274d81af757c30ec2de9cc
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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