HCID 10686621, compound → HCID 10541375, compound

HRID 1107946Notes

Reaction equation

HRID 1107946 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:18])[C:9](Br)=[C:10]([CH3:16])[C:11]=2[N+:13]([O-])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.[CH3:23][OH:24]>[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:18])[CH:9]=[C:10]([CH3:16])[C:11]=2[NH:13][C:23](=[O:24])[C:7]([CH3:12])([CH3:8])[CH3:6])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10686621HCID 10686621, compoundHCID 21584188Chloroform methanol

Product 1

HCID 10541375HCID 10541375, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-Acetyl-5-bromo-4,6-dimethyl-7-nitroindoline (30 g) was dissolved in a mixture (600 ml) of CHCl3 /MeOH=1/1 and 5% Pd-C (5.0 g) was added, which was followed by catalytic hydrogenation at 35° C. The precipitate was collected by filtration together with Pd-C, and dissolved in CHCl3 (300 ml). The mixture was washed with saturated aqueous solution of sodium hydrogencarbonate. The solvent was evaporated under reduced pressure from the filtrate and CHCl3 (300 ml) was added. The mixture was washed with saturated aqueous solution of sodium hydrogencarbonate and combined with the layer of above-mentioned CHCl3. The combined CHCl3 layer was washed with saturated brine and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure and the residue was dissolved in CHCl3 (150 ml). Thereto were successively added at 10° C. pivaloyl chloride (11.7 g) and Et3N (10.8 g). The mixture was stirred at room temperature for 1 hr and CHCl3 (200 ml) was added. The mixture was washed successively with 5% aqueous citric acid and water, and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure and the obtained crude residue was washed with cool Et2O (100 ml) to give 21 g of N-(1-acetyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

  1. additionwas added
  2. customwas followed by catalytic hydrogenation at 35° C
  3. filtrationThe precipitate was collected by filtration together with Pd-C
  4. dissolutiondissolved in CHCl3 (300 ml)
  5. washThe mixture was washed with saturated aqueous solution of sodium hydrogencarbonate
  6. customThe solvent was evaporated under reduced pressure from the filtrate and CHCl3 (300 ml)
  7. additionwas added
  8. washThe mixture was washed with saturated aqueous solution of sodium hydrogencarbonate
  9. washThe combined CHCl3 layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customCHCl3 was evaporated under reduced pressure
  12. dissolutionthe residue was dissolved in CHCl3 (150 ml)
  13. additionThereto were successively added at 10° C. pivaloyl chloride (11.7 g) and Et3N (10.8 g)
  14. additionCHCl3 (200 ml) was added
  15. washThe mixture was washed successively with 5% aqueous citric acid and water
  16. dry with materialdried over anhydrous sodium sulfate
  17. customCHCl3 was evaporated under reduced pressure
  18. customthe obtained crude residue
  19. washwas washed with cool Et2O (100 ml)

Sources & evidence

ORD record
ord-d1fb98aaa67b483a87927ebb1f9c1421
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

Loading…