Triethylamine → HCID 53679748, compound

HRID 1720315Notes

Reaction equation

HRID 1720315 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([C:23]#[CH:24])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:45]>CN(C)C=O.[Pd].[Cu]I>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([C:23]#[C:24][C:43]1[CH:42]=[CH:41][C:40]([Cl:45])=[CH:39][CH:44]=1)=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 127541-Bromo-2-chlorobenzeneHCID 54049466HCID 54049466, compound

Product 1

HCID 53679748HCID 53679748, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 6228DimethylformamideSolvent

Procedure

250 mg of 6-ethinyl-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 8 ml of dimethylformamide with 2 ml of triethylamine, 118 mg of anhydrous potassium carbonate, 22 mg of tetrakis (triphenylphosphine)-palladium(O), 7 mg of copper(I)iodide and 149 mg of 4-bromochlorobenzone and then the mixture is heated for 4 hours to 110° C. Then bromochlorobenzene, copper(I)iodide and palladium catalyst are added again and heated for 3 hours to 120° C. solution temperature. After concentration by evaporation it is taken up in ethyl acetate, washed in succession with saturated sodium carbonate and common salt solution each, dried, filtered and concentrated by evaporation. The residue is chromatographed twice in succession on silica gel, first with the mobile solvent toluene:ethanol:water=80:20:1 and then with the mobile solvent methylene chloride:ethanol=12:1, and the corresponding fractions are combined and used in the next chromatography. 120 mg of 6-(4-chlorophenylethinyl)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, melting point of 220°-221° C., is obtained.

Workup

  1. temperatureis heated for 4 hours to 110° C
  2. temperatureheated for 3 hours to 120° C. solution temperature
  3. concentrationAfter concentration
  4. customby evaporation it
  5. washwashed in succession with saturated sodium carbonate and common salt solution each,
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed twice in succession on silica gel, first with the mobile solvent toluene

Sources & evidence

ORD record
ord-ebb4163673894631bdf9d0cf1be7ad86
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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