Acetic Acid → HCID 19787987, compound

HRID 1656375Notes

Reaction equation

HRID 1656375 reaction equation
[C:1]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]=1[CH2:22][O:23][CH3:24])=[CH:18][C:17]([OH:25])=[CH:16][CH:15]=3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][N:30]=1.C(O)(=O)C>CS(C)=O.C(OCC)(=O)C>[C:1]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]=1[CH2:22][O:23][CH3:24])=[CH:18][C:17]([O:25][C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][N:30]=1)=[CH:16][CH:15]=3)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 693532,5-DibromopyridineHCID 19787989HCID 19787989, compound

Product 1

HCID 19787987HCID 19787987, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

332 mg of 3-benzoyl-6-hydroxy-4-methoxymethyl-beta-carboline and 130 mg of potassium hydroxide powder were mixed in 3 ml of dimethyl sulfoxide under argon with 285 mg of 2,5-dibromopyridine in 1 ml of dimethyl sulfoxide and heated for 1 hour to 90°-95° C. The reaction mixture was poured on ice water, acidified with 1N-acetic acid to pH 5 and shaken out with ethyl acetate. The ethyl acetate phase was washed with saturated common salt solution, dried on magnesium sulfate and concentrated by evaporation. After chromatography on silica gel with dichloromethane/ethyl acetate 1:1 as eluant and recrystallization from the main fraction from ethyl acetate/petroleum ether, the title compound with melting point 193°-194° C. was obtained.

Workup

  1. temperatureheated for 1 hour to 90°-95° C
  2. additionThe reaction mixture was poured on ice water
  3. washThe ethyl acetate phase was washed with saturated common salt solution
  4. customdried on magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customAfter chromatography on silica gel with dichloromethane/ethyl acetate 1:1 as eluant and recrystallization from the main fraction from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-76f7e3da75ed46f2962742e847b2a5dd
Source dataset
uspto-grants-1993_10
Patent number
US05254563

Reaction notes

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