Ammonia → 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1944004Notes

Reaction equation

HRID 1944004 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12](O)=[O:13])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]2=[N:7][CH:8]=1.S(Cl)(Cl)=O.[NH3:29]>C1(C)C=CC=CC=1>[F:1][C:2]([F:23])([F:24])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH2:29])=[O:13])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]2=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 668635175-Trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 668637955-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension, stirred at 20° C., of 1.5 g (4.43 mmol) of 5-trifluoromethyl-1-[(3-fluoro-phenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (WO 2008/093024) in 40 mL of dry toluene are added 3.2 mL (44.34 mmol) of thionyl chloride. The reaction mixture is stirred at reflux for 2 hours and then concentrated under reduced pressure. The resulting product is taken up in 20 mL of dichloromethane and this solution is poured dropwise into a solution of 5.81 mL (44.34 mmol) of 30% aqueous ammonia. The reaction mixture is stirred for 14 hours at 20° C. After this time, a solid is collected by filtration, and is triturated in 50 mL of diisopropyl ether. After filtering off and drying under reduced pressure, 1.5 g of the expected product are collected.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. stirringThe reaction mixture is stirred for 14 hours at 20° C
  4. filtrationAfter this time, a solid is collected by filtration
  5. customis triturated in 50 mL of diisopropyl ether
  6. filtrationAfter filtering off
  7. dry with materialdrying under reduced pressure, 1.5 g of the expected product
  8. customare collected

Sources & evidence

ORD record
ord-876f3b29b57a4f839f5561c78eb15d8e
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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