Pyridine → HCID 10755750, compound

HRID 865650Notes

Reaction equation

HRID 865650 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:23][CH2:24][C:25](Cl)=[O:26]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:25](=[O:26])[CH2:24][Cl:23])=[CH:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 111066586-(4-FLUOROPHENYL)INDOLE

Product 1

HCID 10755750HCID 10755750, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution under N2 of 6-(4-fluorophenyl)indole (10.0 g, 47.4 mmol) in dioxane (36 mL) was added pyridine (5.80 mL, 71.8 mmol) and the solution was heated to 60° C. A solution of chloroacetyl chloride (5.66 mL, 71.1 mmol) in dioxane (12.5 mL) was added over one hour. The reaction mixture was stirred for one hour at 60° C., then was cooled to ambient temperature and partitioned between H2O and ether. The resulting orange precipitate was filtered off, recrystallized from ethanol, and rinsed with cold ether to give 6-(4-fluorophenyl)-3-chloroacetylindole (2.78 g, 20% as an orange solid.

Workup

  1. temperaturewas cooled to ambient temperature
  2. custompartitioned between H2O and ether
  3. filtrationThe resulting orange precipitate was filtered off
  4. customrecrystallized from ethanol
  5. washrinsed with cold ether

Sources & evidence

ORD record
ord-87c6c74a5aef4a2fa041263859803ba5
Source dataset
uspto-grants-1996_10
Patent number
US05567711

Reaction notes

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