Water → HCID 67354184, compound

HRID 2405100Notes

Reaction equation

HRID 2405100 reaction equation
[CH3:1][S:2][CH2:3][N:4]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:9]=[CH:8][C:7]=2[CH:6]=[CH:5]1.[OH:20]OS([O-])=O.[K+].[OH2:26]>CO>[CH3:1][S:2]([CH2:3][N:4]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:9]=[CH:8][C:7]=2[CH:6]=[CH:5]1)(=[O:20])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 67356941HCID 67356941, compound

Product 1

HCID 67354184HCID 67354184, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 1-(methylthiomethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (8A, 920 mg, 3.3 mmol) and Oxone (4.2 g, 6.8 mmol) in MeOH:H2O=1:1 (20 ml) was stirred at room temperature for 2 h. The mixture was extracted with EtOAc:H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was purified by chromatography (SiO2, EtOAc) to give tert-butyl 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (8B, 820 mg, 80% yield) as a colorless amorphous. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.70 (s, 9H) 2.75 (s, 3H) 5.40 (s, 2H) 6.88 (dd, J=3.41, 0.88 Hz, 1H) 7.50 (d, J=3.54 Hz, 1H) 8.21 (s, 1H) 9.09 (d, J=1.01 Hz, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-44cb3ea25eb544eaa6628ebd31ab0840
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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