4-Fluorobenzoyl chloride → HCID 67675578, compound

HRID 363337Notes

Reaction equation

HRID 363337 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]3[CH2:19][CH:18]4[N:14]([CH2:15][CH2:16][CH2:17]4)[CH2:13][CH:12]=3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>N1C=CC=CC=1>[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:10]2[C:5]3[C:6](=[N:7][C:2]([NH2:1])=[CH:3][CH:4]=3)[C:8]([C:11]3[CH2:19][CH:18]4[N:14]([CH2:15][CH2:16][CH2:17]4)[CH2:13][CH:12]=3)=[CH:9]2)=[O:26])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 54097799HCID 54097799, compound

Product 1

HCID 67675578HCID 67675578, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 0.10 gm (0.39 mMol) 5-amino-3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)pyrrolo[3,2-b]pyridine and 0.56 μL (0.47 mMol) 4-fluorobenzoyl chloride in 10 mL pyridine was stirred at 55° C. for 18 hours. The reaction mixture was then partitioned between 1N sodium hydroxide and 3:1 chloroform:isopropanol. The phases were separated and the organic phase washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to radial chromatography (2 mm silica plate) eluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 0.077 gm (57%) of the title compound. The title compound was recrystallized twice from ethanol:water and dried under reduced pressure to provide a sample for analysis.

Workup

  1. customThe reaction mixture was then partitioned between 1N sodium hydroxide and 3:1 chloroform
  2. customThe phases were separated
  3. washthe organic phase washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with dichloromethane containing 10% methanol and 1% ammonium hydroxide
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f0a174d312f4bb3922660e4cd200fd6
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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