Triethylamine → HCID 86743465, compound

HRID 2352073Notes

Reaction equation

HRID 2352073 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[N:14]([CH2:23][CH2:24][CH3:25])[C:13]=3I)[N:9]([CH3:27])[CH2:8]1)=[O:5])[CH3:2].[CH2:30](N(CC)CC)[CH3:31].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([Si](C)(C)C)=C>CN(C)C=O.[Pd](Cl)Cl>[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[N:14]([CH2:23][CH2:24][CH3:25])[C:13]=3[CH:30]=[CH2:31])[N:9]([CH3:27])[CH2:8]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 79102VinyltrimethylsilaneHCID 80271Tri-o-tolylphosphineHCID 13799217HCID 13799217, compound

Product 1

HCID 86743465HCID 86743465, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

In a small autoclave, 1.15 g of 1,1-diethyl-3-(2-iodo-1-propyl-6-methyl-8α-ergolinyl)urea is heated under argon for 3 hours to a bath temperature of 115° C. in 10 ml of dimethylformamide with 10 ml of triethylamine, 53.5 mg of triorthotolylphosphine, 39.4 mg of palladium(II) chloride and 1.34 ml of vinyltrimethylsilane. After evaporation, the mixture is distributed in methylene chloride/sodium bicarbonate solution. The organic phase is evaporated and chromatographed over silica gel with ethyl acetate: ethanol=3:1 as the eluent, thus obtaining 218 mg of 1,1-diethyl-3-(2-trimethylsilylvinyl-1-propyl-6-methyl-8α-ergolinyl)urea and 230 mg of 1,1-diethy-3-(2-vinyl-1-propyl-6-methyl-8α-ergolinyl)urea as oils.

Workup

  1. customAfter evaporation
  2. customThe organic phase is evaporated
  3. customchromatographed over silica gel with ethyl acetate

Sources & evidence

ORD record
ord-d7e8b27d4cf54f86bf28f6b2818d0e4e
Source dataset
uspto-grants-1989_10
Patent number
US04874768

Reaction notes

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