Sodium Thiosulfate → HCID 86703314, compound

HRID 2409997Notes

Reaction equation

HRID 2409997 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH:2]([C:3]1[N:8]=[C:7]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:6]=[CH:5][CH:4]=1)=[O:1]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86703313HCID 86703313, compound

Product 1

HCID 86703314HCID 86703314, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(6-hydroxymethylpyridin-2-ylmethyl)-6-methoxy-2-phenyl-1H-indole-1-carboxylate (600 mg) in dichloromethane (6 mL) was added Dess-Martin periodinane (744 mg), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1 mol/L aqueous sodium thiosulfate solution, followed by stirring for 5 minutes. The mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (486 mg). 1H-NMR (CDCl3) δ ppm: 1.23 (9H, s), 3.89 (3H, s), 4.15 (2H, s), 6.84 (1H, dd, J=2.3, 8.7 Hz), 7.15-7.21 (1H, m), 7.28-7.44 (6H, m), 7.61-7.69 (1H, m), 7.72-7.77 (1H, m), 7.86 (1H, d, J=2.3 Hz), 10.02-10.05 (1H, m).

Workup

  1. stirringby stirring for 5 minutes
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-985f3498938e477a8908bb4f5d40da99
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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