Diethylamine → HCID 13136240, compound

HRID 1903116Notes

Reaction equation

HRID 1903116 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][CH3:20])=[CH:15][C:14](Br)=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(NCC)C.[CH3:27][N:28]([CH3:32])[CH2:29][C:30]#[CH:31]>[Cl-].[Cl-].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[Pd+2].CN1CCCC1=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][CH3:20])=[CH:15][C:14]([C:31]#[C:30][CH2:29][N:28]([CH3:32])[CH3:27])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 81643N,N-DimethylpropargylamineHCID 13037329HCID 13037329, compound

Product 1

HCID 13136240HCID 13136240, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 9875586Bis(tri-o-tolylphosphine)palladium(II) DichlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

347 mg of 6-bromo-4-ethyl-beta-carboline-3-carboxylic-acid-ethylester, 32 mg of palladium-bis-(tri-o-tolylphosphine)-dichloride, 32 mg of cuprous iodide, 5 ml of diethylamine, 5 ml of N-methyl-2-pyrrolidone and 250 mg of 3-dimethylamino-1-propine are heated anhydrously and under nitrogen for 7.5 h at 80°-90° C. After concentration in an oil pump vacuum, the residue is chromatographed on 30 g of silica gel with methylene-chloride/methanol (10/2) as the eluant. The correspondingly consolidated fractions are separated by preparative film chromatography and 170 mg of 6-(3-dimethylamino-1-propinyl)-4-ethyl-beta-carboline-3-carboxylic-acid-ethylester is obtained in the form of an oil.

Workup

  1. concentrationAfter concentration in an oil pump vacuum
  2. customthe residue is chromatographed on 30 g of silica gel with methylene-chloride/methanol (10/2) as the eluant
  3. customThe correspondingly consolidated fractions are separated by preparative film chromatography

Sources & evidence

ORD record
ord-eedc684e5883449a8bf9875fd9980162
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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