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N-BOC-ethylenediamine → N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)ethylenediamine

HRID 10505
Notes
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Reaction equation

HRID 10505 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:33]([O:37][C:38](=[O:43])[NH:39][CH2:40][CH2:41][NH2:42])([CH3:36])([CH3:35])[CH3:34].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:33]([O:37][C:38]([NH:39][CH2:40][CH2:41][NH:42][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)=[O:43])([CH3:36])([CH3:35])[CH3:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 187201N-BOC-ethylenediamineHCID 7364875-BromoisoquinolineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 21979917N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)ethylenediamineYield 70%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (416 mg, Spex), tris(dibenzylideneacetone)dipalladium(0) (92 mg), 2-(di-tert-butylphosphino)biphenyl (119 mg), N-(2-aminoethyl)carbamic acid tert-butyl ester (385 mg) and sodium tert-butoxide (269 mg) in toluene (5 ml) was stirred with heating at 80° C. for 2 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (5 ml). The insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (402 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble matters were removed by filtration through Celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-236c7339795b45e393f5e303add9f945
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094789B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes