Hydrochloric Acid → HCID 20262412, compound

HRID 371099Notes

Reaction equation

HRID 371099 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C1C=CC=CC=1>[C:17]([N:1]1[CH:6]=[CH:5][CH:4]([C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[C:8]([F:7])[CH:9]=3)[NH:13][CH:12]=2)[CH:3]=[CH:2]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 678615-Fluoroindole

Product 1

HCID 20262412HCID 20262412, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture of 100 parts of pyridine, 53 parts of 5-fluoro-1H-indole and 270 parts of benzene were added dropwise 57 parts of benzoyl chloride. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured onto a dilute hydrochloric acid solution and the layers were separated. The organic phase was dried, filtered and evaporated. The residue was purified twice by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 80 parts of 1-benzoyl-4-(5-fluoro-1H-indol-3-yl)-1,4-dihydropyridine as a residue (intermediate 19).

Workup

  1. customthe layers were separated
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified twice by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-c08d95374f534793bec5a4cff122f196
Source dataset
uspto-grants-1985_07
Patent number
US04529727

Reaction notes

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