Triethylamine → HCID 54049466, compound

HRID 1720313Notes

Reaction equation

HRID 1720313 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](I)=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].C[Si]([C:28]#[CH:29])(C)C.C(N(CC)CC)C>CN(C)C=O.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[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:28]#[CH:29])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 54360890HCID 54360890, compound

Product 1

HCID 54049466HCID 54049466, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2.1 g of 6-iodo-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 30 ml of dimethylformamide in succession with 1.53 ml of trimethylsilylacetylene, 15 ml of triethylamine, 50 mg of copper (I) iodide and 100 mg of tetrakis (triphenylphosphine)-palladium (O) and heated for 3 hours under argon to 60° C. solution temperature. After removal of the solvent the residue is taken up in ethyl acetate and in succession is washed with saturated sodium bicarbonate and common salt solution. The organic phase was dried, filtered and concentrated by evaporation and the residue is chromatographed on silica gel with methylene chloride:ethanol=12:1. The correspondingly combined fractions are stirred for 1 hour in 50 ml of methylene chloride with 4 ml of tetrabutylammonium fluoride at room temperature. The solution is washed with water, dried, filtered and concentrated by evaporation and the residue is chromatographed on silica gel with methylene chloride:ethanol=10:1. 830 mg of 6-ethinyl-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, melting point 191°- 193° C. (ethyl acetate/hexane) is obtained by the corresponding combination of the fractions.

Workup

  1. customAfter removal of the solvent the residue
  2. washis washed with saturated sodium bicarbonate and common salt solution
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customthe residue is chromatographed on silica gel with methylene chloride
  7. washThe solution is washed with water
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation
  11. customthe residue is chromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-3f27315771ec4f93a0f061d6e7c998b9
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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