Dimethylformamide → HCID 68555827, compound

HRID 2382075Notes

Reaction equation

HRID 2382075 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH3:13].C[N:15](C=O)C>>[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([NH2:15])[CH:10]=[C:9]2[CH3:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 55287812HCID 55287812, compound

Product 1

HCID 68555827HCID 68555827, compound

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (805 mg, 20.1 mmol, 60% in mineral oil) in DMF (5 mL) at 0° C. is treated with 7-fluoro-3-methylindole (200 mg, 1.34 mmol) and stirred at 0° C. for 1 h. The mixture is treated with HOSA (757 mg, 6.7 mmol) portion wise and warmed to rt over 2 h. 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 7-fluoro-3-methyl-indol-1-ylamine, which is used in the next step without further purification.

Workup

  1. additionThe mixture is treated with HOSA (757 mg, 6.7 mmol) portion wise
  2. temperaturewarmed to rt over 2 h
  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-5ea731272e804ea1aa4faaaecb791eef
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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