Dimethylformamide → HCID 68555193, compound

HRID 2382072Notes

Reaction equation

HRID 2382072 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:14])=[CH:8]2.C[N:16](C=O)C>>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([NH2:16])[C:9]([CH3:14])=[CH:8]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 706425-Methoxy-2-methylindole

Product 1

HCID 68555193HCID 68555193, compound

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (1.25 g, 51 mmol, 60% in mineral oil) in DMF (47 mL) at 0° C. is treated with 5-methoxy-2-methylindole (500 mg, 3.1 mmol) and stirred at 0° C. for 0.5 h. The mixture is treated with HOSA (1.92 g, 17.0 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice, and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo to afford 5-methoxy-2-methyl-indol-1-ylamine, which is used in the next step without further purification.

Workup

  1. additionThe mixture is treated with HOSA (1.92 g, 17.0 mmol) portion wise
  2. temperaturewarmed to rt over 2 h
  3. additionThe mixture is then poured over ice
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1331166a1e74509971a594c8e6834b6
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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