Chloromethyl methyl sulfide → HCID 67356941, compound

HRID 2405099Notes

Reaction equation

HRID 2405099 reaction equation
[NH:1]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Cl[CH2:20][S:21][CH3:22]>CN(C=O)C>[CH3:20][S:21][CH2:22][N:1]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 57763153HCID 57763153, compound

Product 1

HCID 67356941HCID 67356941, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tert-butyl 1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1.0 g, 4.6 mmol) in DMF (20 ml) was added sodium hydride (60% in oil) (0.41 g, 10 mmol) and stirred at room temperature for 3 h. To the mixture, (chloromethyl)(methyl)sulfane (0.89 g, 9.2 mmol) was added and stirred at room temperature for 2 h. The reaction 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, hexanes:EtOAc=50:50) to give tert-butyl 1-(methylthiomethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (8A, 920 mg, 3.3 mmol, 72% yield) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.61 (s, 9H) 1.94 (s, 3H) 5.15 (s, 2H) 6.64 (d, J=3.28 Hz, 1H) 7.34 (d, J=3.28 Hz, 1H) 8.15 (s, 1H) 8.93 (d, J=1.01 Hz, 1H).

Workup

  1. stirringstirred at room temperature for 2 h
  2. extractionThe reaction mixture was extracted with EtOAc/H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by chromatography (SiO2, hexanes:EtOAc=50:50)

Sources & evidence

ORD record
ord-c9d4471f21be4ed9953a57c4f92a63e3
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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