Dimethylformamide → HCID 68552093, compound

HRID 2382047Notes

Reaction equation

HRID 2382047 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C[N:22](C=O)C>>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH2:22])[CH:8]=[C:7]2[CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 685543805-fluoro-3-(2-pyridin-3-yl-ethyl)-1H-indole

Product 1

HCID 68552093HCID 68552093, compound

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (600 mg, 15 mmol, 60% in mineral oil) in DMF (10 mL) at 0° C. is treated with 5-fluoro-3-(2-pyridin-3-yl-ethyl)-1H-indole (240 mg, 1 mmol) and stirred at 0° C. for 0.5 h. The mixture is treated with HOSA (565 mg, 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 (3×1050 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo to afford 5-fluoro-3-(2-pyridin-3-yl-ethyl)-indol-1-ylamine, which is used in the next step without further purification.

Workup

  1. additionThe mixture is treated with HOSA (565 mg, 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 (3×1050 mL)
  6. dry with materialThe combined organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8165698bb88149cf84592fd74d537e08
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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