Hydrochloric Acid → Methyl 7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate

HRID 1188908Notes

Reaction equation

HRID 1188908 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7]2.Cl.O.[C:28](OCC)(=O)C>CO>[CH3:28][O:1][C:2]1[CH:3]=[C:4]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 66897290Methyl 7-hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate

Product 1

HCID 67118469Methyl 7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 7-hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.1 g) was dissolved in a mixture of ethyl acetate (20 mL) and methanol (5 mL). The mixture was cooled to 0° C., and 2M trimethylsilyldiazomethane diethyl ether solution (2 mL) was added dropwise to the mixture. The mixture was stirred at 0° C. for 30 min, and then 2M trimethylsilyldiazomethane diethyl ether solution (0.5 mL) was added dropwise to the mixture again. After stirring at 0° C. for 30 min, 1M hydrochloric acid (1 mL) was added to the mixture to quench the reaction. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual oil was solidified with diethyl ether to give the title compound (0.99 g, 88%) as a pale orange solid. MS 377 (MH+).

Workup

  1. stirringAfter stirring at 0° C. for 30 min
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7908a65f66cc47069a97dc89a51d8842
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…