Dimethylformamide → HCID 68554564, compound

HRID 2382036Notes

Reaction equation

HRID 2382036 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:19])[C:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[NH:11][CH:10]=1)([CH3:8])[CH3:7].C[N:21](C=O)C>>[CH3:3][O:4][C:5](=[O:19])[C:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]([NH2:21])[CH:10]=1)([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 68556856HCID 68556856, compound

Product 1

HCID 68554564HCID 68554564, compound

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (1.02 g, 25.5 mmol, 60% in mineral oil) in DMF (25 mL) at 0° C. is treated with 2-(5-fluoro-1H-indol-3-yl)-2-methyl-propionic acid methyl ester (400 mg, 1.7 mmol) and stirred at 0° C. for 0.5 h. The mixture is treated with HOSA (960 mg, 8.5 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice, filtered through a pad of Celite, and extracted with EtOAc (3×100 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo to afford 2-(1-amino-5-fluoro-1H-indol-3-yl)-2-methyl-propionic acid methyl ester, which is used in the next step without further purification.

Workup

  1. additionThe mixture is treated with HOSA (960 mg, 8.5 mmol) portion wise
  2. temperaturewarmed to rt over 2 h
  3. additionThe mixture is then poured over ice
  4. filtrationfiltered through a pad of Celite
  5. extractionextracted with EtOAc (3×100 mL)
  6. dry with materialThe combined organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69ec8050458b4a28b9148f36c7ce701b
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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