2-Iodoxybenzoic acid → HCID 21099275, compound

HRID 1351739Notes

Reaction equation

HRID 1351739 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[C:6]2[C:10]=1[NH:9][C:8]1[C:11]([CH2:18][CH2:19][OH:20])([CH2:15][CH2:16][CH3:17])[O:12][CH2:13][CH2:14][C:7]2=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[O:22])=[C:6]2[C:10]=1[NH:9][C:8]1[C:11]([CH2:18][CH:19]=[O:20])([CH2:15][CH2:16][CH3:17])[O:12][CH2:13][CH2:14][C:7]2=1

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 21099269HCID 21099269, compound

Product 1

HCID 21099275HCID 21099275, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The mixture of [8-fluoro-1-(2-hydroxy-ethyl)-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-5-yl]-morpholin-4-yl-methanone (100 mg, 0.256 mmol) and o-iodoxybenzoic acid (IBX, 430 mg, 1.54 mmol) in DMSO (3.5 mL) was stirred overnight at room temperature. The solution was diluted with H2O (7 mL) and the precipitates were filtered and the filter cake was rinsed with EtOAc. The filtrate was extracted with EtOAc (3×10 mL) and the combined organic solution was washed with brine (20 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 60% EtOAc in hexanes) to give 89 mg (90%) of the title compound as a pale yellow solid. 1H NMR (CDCl3): 300 MHz δ 9.75 (bs, 1H), 9.05 (bs, 1H), 6.89 (m, 2H), 4.00–2.64 (m, 14H), 1.89 (m, 1H), 1.63 (s, 1H), 1.26 (m, 2H), 0.88 (t, J=5.49 Hz, 3H).

Workup

  1. filtrationthe precipitates were filtered
  2. washthe filter cake was rinsed with EtOAc
  3. extractionThe filtrate was extracted with EtOAc (3×10 mL)
  4. washthe combined organic solution was washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica, 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0b87b4b10dd6424e864fe90219ef5fd3
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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