Methyl acetoacetate → 7-amino-1,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid methyl ester

HRID 2183551Notes

Reaction equation

HRID 2183551 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[CH3:15])=[CH:5][N:4]([CH3:16])[C:3]=1[C:17]#[N:18].[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.Cl[Sn](Cl)(Cl)Cl>ClCCCl>[CH3:26][O:25][C:19]([C:20]1[C:17]([NH2:18])=[C:3]2[N:4]([CH3:16])[CH:5]=[C:6]([C:7]3[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=3[CH3:15])[C:2]2=[N:1][C:21]=1[CH3:23])=[O:24]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 24287Tin tetrachlorideHCID 224744433-amino-1-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole-2-carbonitrile

Product 1

HCID 540437777-amino-1,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-amino-1-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole-2-carbonitrile (2 mmol), methyl acetoacetate (4 mmol) and SnCl4 (4 mmol) in 1,2-dichloroethane was heated at reflux for about six hours until all the starting material were consumed. The mixture was quenched with acetone, basified with saturated NaHCO3, then filtered through Celite?. The filtrate was concentrated to dryness. The residue was quenched with water and extracted with chloroform. The chloroform layer was washed with brine, dried and concentrated to dryness to give 7-amino-1,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid methyl ester. The product may be purified by trituration.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about six hours until all the starting material
  3. customwere consumed
  4. customThe mixture was quenched with acetone
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated to dryness
  7. customThe residue was quenched with water
  8. extractionextracted with chloroform
  9. washThe chloroform layer was washed with brine
  10. customdried
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3eaa85f08312493d9154aff17c0376f7
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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