2-Iodoxybenzoic acid → HCID 85892012, compound

HRID 1351741Notes

Reaction equation

HRID 1351741 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4]([CH2:12][CH2:13][OH:14])=[CH:5][NH:6]2.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4]([CH2:12][CH:13]=[O:14])=[CH:5][NH:6]2

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 23401455HCID 23401455, compound

Product 1

HCID 85892012HCID 85892012, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The mixture of 2-(4-bromo-7-fluoro-1H-indol-3-yl)-ethanol (3.00 g, 11.6 mmol) and o-iodoxybenzoic acid (IBX, 9.76 g, 34.9 mmol) in DMSO (60 mL) was stirred overnight at room temperature. The solution was diluted with H2O (100 mL) and the precipitates were filtered and the filter cake was rinsed with EtOAc. The filtrate was extracted with EtOAc (3×150 mL) and the combined organic solution was washed with brine (300 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 25% EtOAc in hexanes) to give 2.48 g (83%) of the title compound as a pale yellow solid. 1H NMR (CDCl3): 300 MHz δ 9.93 (s, 1H), 8.44 (bs, 1H), 7.20 (m, 1H), 7.17 (dd, J=8.40, 4.32 Hz, 1H), 6.80 (dd, J=10.2, 8.40 Hz, 1H), 4.12 (s, 2H).

Workup

  1. filtrationthe precipitates were filtered
  2. washthe filter cake was rinsed with EtOAc
  3. extractionThe filtrate was extracted with EtOAc (3×150 mL)
  4. washthe combined organic solution was washed with brine (300 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica, 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d169863a8b46471a980d471771f8e19f
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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