Ammonia → 3-Amino-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

HRID 1035839Notes

Reaction equation

HRID 1035839 reaction equation
[NH3:1].Cl[C:3]1([C:16]2[C:17]([O:22][CH2:23][CH3:24])=[N:18][CH:19]=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][C:4]1=[O:15].[Na+].[Cl-]>ClCCl>[NH2:1][C:3]1([C:16]2[C:17]([O:22][CH2:23][CH3:24])=[N:18][CH:19]=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][C:4]1=[O:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 67087558HCID 67087558, compound

Product 1

HCID 670874773-Amino-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.4 ml (17.0 mmol) of a 7N methanolic ammonia solution were added dropwise to a cooled solution of 1.13 g (3.41 mmol) of 3-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile in 20 ml of dichloromethane under a nitrogen atmosphere, and the reaction mixture was then stirred at room temperature overnight. The reaction mixture was mixed with saturated NaCl solution and extracted with ethyl acetate (3×). The combined organic phases were dried over magnesium sulfate and filtered, and the solvent was removed in vacuo. The residue was mixed with 20 ml of diethyl ether. After stirring for 5 min, a white solid precipitated and was filtered off and dried in a vacuum oven. 800 mg of the title compound were obtained as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. additionThe residue was mixed with 20 ml of diethyl ether
  6. stirringAfter stirring for 5 min
  7. customa white solid precipitated
  8. filtrationwas filtered off
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-79d4a8c4888e41388e3bb4e0e0758ee0
Source dataset
uspto-grants-2013_10
Patent number
US08546401B2

Reaction notes

Loading…