Hydrochloric Acid → HCID 60035418, compound

HRID 1253834Notes

Reaction equation

HRID 1253834 reaction equation
[BH4-].[Li+].[NH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]2[N:11]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=3[CH3:24])[C:12](=O)[CH:13]([CH3:14])[C:5]=12.Cl.[OH-].[Na+]>O1CCCC1>[Cl:23][C:19]1[CH:18]=[C:17]([CH3:24])[C:16]([N:11]2[C:6]3=[N:7][C:8]([CH3:10])=[CH:9][C:4]([NH2:3])=[C:5]3[C:13]([CH3:14])=[CH:12]2)=[C:21]([CH3:22])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 60035535HCID 60035535, compound

Product 1

HCID 60035418HCID 60035418, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium borohydride (11.6 g) in tetrahydrofuran (50 mL) was added a solution of 4-amino-1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (33.7 g) in tetrahydrofuran (100 mL) was added. The mixture was stirred at reflux for 1 hour. After cooling with ice-cooling bath, a 6M HCl aqueous solution was added slowly. The solution was made to alkaline (pH=9) with 4 M NaOH aqueous solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=3:1) to give 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine (17.9 g) as a solid.

Workup

  1. additionwas added
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling with ice-
  4. temperaturecooling bath
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b65981b34412451eb2a237ad7a177866
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

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