Dimethylformamide → HCID 68555546, compound

HRID 2382078Notes

Reaction equation

HRID 2382078 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH3:16])(=[O:6])=[O:5].C[N:18](C=O)C>>[CH3:3][S:4]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([NH2:18])[CH:11]=[C:10]2[CH3:16])(=[O:6])=[O:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 68555576HCID 68555576, compound

Product 1

HCID 68555546HCID 68555546, compound

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (1.06 g, 26.6 mmol, 60% in mineral oil) in DMF (15 mL) at 0° C. is treated with 5-methanesulfonyl-3-methyl-1H-indole (370 mg, 1.77 mmol) and stirred at 0° C. for 1 h. The mixture is treated with HOSA (1 g, 8.85 mmol) portion wise and warmed to rt overnight. The mixture is then poured over ice, and extracted with EtOAc (3×100 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo to afford 5-methanesulfonyl-3-methyl-indol-1-ylamine, which is used in the next step without further purification.

Workup

  1. additionThe mixture is treated with HOSA (1 g, 8.85 mmol) portion wise
  2. temperaturewarmed to rt overnight
  3. additionThe mixture is then poured over ice
  4. extractionextracted with EtOAc (3×100 mL)
  5. dry with materialThe combined organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ef17d42466443d5a225bf96948c71f5
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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