Toluene → HCID 71258387, compound

HRID 1506233Notes

Reaction equation

HRID 1506233 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][N:5]=[C:4]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:3]=12.C1(C)C=CC=CC=1.[NH3:29].CO.[Cl-].[Na+]>S(Cl)(Cl)=O>[Cl:1][C:2]1[C:7]([C:8]([NH2:29])=[O:9])=[CH:6][N:5]=[C:4]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:3]=12

Participants

6

Reactant 4

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 21705897Ammonia methanolHCID 59292039HCID 59292039, compound

Product 1

HCID 71258387HCID 71258387, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (480 mg, 1.47 mmol) in thionyl chloride (3 mL) was stirred at room temperature for 2 hours. After addition of toluene, the reaction mixture was concentrated under reduced pressure, and after addition of toluene, concentrated under reduced pressure. The residue was dissolved in dichloromethane (5 mL), and ammonia-methanol solution (7.0 M, 1.0 mL, 7.0 mmol) was added dropwise, and the resulting reaction mixture was stirred for 1 hour. After addition of saturated aqueous sodium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a colorless solid (461 mg, yield 96%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of toluene
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  5. customthe resulting reaction mixture
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08d723a1e67d4862b36c723725d361dd
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…