Hydrochloric Acid → HCID 13476527, compound

HRID 1156334Notes

Reaction equation

HRID 1156334 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[CH:10][CH:9]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O>[C:17]([N:1]1[CH:6]=[CH:5][CH:4]([C:12]2[C:11]3[C:15](=[CH:16][C:8]([F:7])=[CH:9][CH:10]=3)[NH:14][CH:13]=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 3512786-Fluoroindole

Product 1

HCID 13476527HCID 13476527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 250 parts of pyridine and 39 parts of 6-fluoro-1H-indole are added dropwise 42 parts of benzoyl chloride at 22° C. Upon completion, stirring is continued for 2 hours at room temperature. The reaction mixture is diluted with water and a hydrochloric acid solution 2 N is added. The product is extracted twice with 350 parts of 1,1'-oxybisethane. The combined extracts are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 95 parts of 1-benzoyl-4-(6-fluoro-1H-indol-3-yl)-1,4-dihydropyridine as an oily residue.

Workup

  1. extractionThe product is extracted twice with 350 parts of 1,1'-oxybisethane
  2. customThe combined extracts are dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated

Sources & evidence

ORD record
ord-f0dfb437fab24bd59010ca2169b12007
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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