Ammonia → HCID 14723155, compound

HRID 2247881Notes

Reaction equation

HRID 2247881 reaction equation
Br[C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:7][NH:6]1.[CH2:26](B(CC)CC)[CH3:27].[OH-].[K+].Cl.N>C1(C)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:21]([N:20]([CH2:23][CH3:24])[C:19]([NH:18][C@H:8]1[CH2:9][C@H:10]2[C@@H:5]([CH2:4][C:3]3[C:17]4[C:15](=[CH:14][CH:13]=[CH:12][C:11]2=4)[NH:16][C:2]=3[CH2:26][CH3:27])[NH:6][CH2:7]1)=[O:25])[CH3:22]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7357TriethylboraneHCID 14797Potassium HydroxideHCID 86744963HCID 86744963, compound

Product 1

HCID 14723155HCID 14723155, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Procedure

1.00 g (2.47 mmol) of 3-(2-bromo-8α-ergolinyl)-1,1-diethylurea is dissolved in 10 ml of toluene, mixed with 90 mg (0.12 mmol) of 1,1'-bis(diphenylphosphino)-ferrocene palladium(II) chloride and stirred for 15 minutes at room temperature. Then 5.5 ml of triethylborane (1M solution in tetrahydrofuran) and 2.5 ml of 4N potassium hydroxide solution are added and the mixture is refluxed for 4 hours. The reaction mixture is acidified with 2N hydrochloric acid, made alkaline with concentrated ammonia and extracted with dichloromethane. The raw product, obtained after drying of the organic phases (sodium sulfate) and removal of the solvent in a vacuum, is chromatographed on silica gel. (dichloromethane/methanol 98:2). Yield after crystallization (ethyl acetate): 307 mg (35%) [α]D +47.6° (c=0.5 in chloroform).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-908194681b254a9c826f6830d81aa58d
Source dataset
uspto-grants-1991_08
Patent number
US05037832

Reaction notes

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