Triacetoxyperiodinane → 4-bromo-6-fluoro-1H-indole-2-carbaldehyde

HRID 857396Notes

Reaction equation

HRID 857396 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:12][OH:13])[NH:6]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:12]=[O:13])[NH:6]2

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 21867424(4-Bromo-6-fluoro-1h-indol-2-yl)methanol

Product 1

HCID 218674094-bromo-6-fluoro-1H-indole-2-carbaldehydeYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-6-fluoro-1H-indol-2-yl)methanol (2.6 g, 11 mmol) in CH2Cl2 (100 mL) at r.t. was added Dess-Martin periodinane (6.4 g, 15 mmol). The mixture was stirred for 30 minutes at r.t. and saturated aqueous NaHCO3 was added. The mixture was filtered through a celite pad and the filtrate was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 30% EtOAc to give 2 g of the title compound.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. extractionthe filtrate was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 30% EtOAc

Sources & evidence

ORD record
ord-49b74c27129543fab486e5ccd6091524
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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