Ethanol → HCID 19996582, compound

HRID 2248471Notes

Reaction equation

HRID 2248471 reaction equation
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14](Br)=[C:13]3[CH2:19][CH:20]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:21][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([OH:31])C.[C]=[O:33].C(N([CH2:39][CH3:40])CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([C:29]([O:31][CH2:39][CH3:40])=[O:33])=[C:13]3[CH2:19][CH:20]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:21][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 54284979HCID 54284979, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 19996582HCID 19996582, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

Into a 500-ml autoclave were added 1-benzoyl-4-(trifluoroacetyl)amino-6-bromo-1,2,2a,3,4, 5-hexahydrobenz[cd]indole (453 mg, 1 mmole) bis,(triphenylphosphine)palladium chloride (50 mg) triethylamine (0.5 ml) and ethanol (200 ml). The autoclave was purged three times to 60 psig (4.22 Kg per square cm) with carbon monoxide and then pressurized to 100 psig (7.03 Kg per square cm) at room temperature. The mixture was heated to 120° C. and maintained at temperature for about 2 hours during which time the pressure increased to about 140 psig (9.84 Kg per square cm). The vessel was cooled, vented and opened to provide a clear solution. High pressure liquid chromatography of the reaction mixture showed only starting material and no reaction products. The reaction mixture was returned to the autoclave. An additional 0.5 ml of triethylamine was added along with 50 mg of bis(triphenylphosphine)palladium chloride. The autoclave was vented three times with carbon monoxide, pressured to 100 psig (7.03 Kg per square cm) and heated to 145° C. The pressure increased to 160 psig (11.25 Kg per square cm). The reaction mixture was maintained at about 130° C. overnight after cooling. Analysis of the reaction mixture by high pressure liquid chromatography showed essentially all of the starting material remained with only minor peaks corresponding to other materials present.

Workup

  1. customThe autoclave was purged three times to 60 psig (4.22 Kg per square cm) with carbon monoxide
  2. custompressurized to 100 psig (7.03 Kg per square cm) at room temperature
  3. temperaturemaintained at temperature for about 2 hours during which time the pressure
  4. temperatureincreased to about 140 psig (9.84 Kg per square cm)
  5. temperatureThe vessel was cooled
  6. customto provide a clear solution
  7. temperatureheated to 145° C
  8. temperatureThe pressure increased to 160 psig (11.25 Kg per square cm)
  9. temperatureThe reaction mixture was maintained at about 130° C. overnight
  10. temperatureafter cooling

Sources & evidence

ORD record
ord-f334a80ecca64a73ba11c8739186959b
Source dataset
uspto-grants-1991_08
Patent number
US05039820

Reaction notes

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