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Acetonitrile → 7-[3-(2-Methyl-1H-indol-4-yloxy)-propyl]-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40644
Notes
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Reaction equation

HRID 40644 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([CH3:15])[NH:10]2.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[N:26]1[CH2:33][C@H:32]2[NH:34][CH2:35][C@@H:27]1[CH2:28][CH:29]=[CH:30][CH2:31]2.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.C(OCC)(=O)C>[CH3:15][C:9]1[NH:10][C:11]2[C:7]([CH:8]=1)=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:34]1[CH2:35][CH:27]3[N:26]([C:17]4[CH:18]=[CH:19][C:20]5[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:16]=4)[CH2:33][CH:32]1[CH2:31][CH:30]=[CH:29][CH2:28]3)[CH:14]=[CH:13][CH:12]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 59686818Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-eneHCID 692351584-(3-Chloro-propoxy)-2-methyl-1H-indole

Product 1

HCID 692335407-[3-(2-Methyl-1H-indol-4-yloxy)-propyl]-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Chloro-propoxy)-2-methyl-1H-indole (0.16 g, 0.72 mmol), Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (0.1 g, 0.38 mmol), K2CO3 (72 mg, 0.52 mmol), acetonitrile (30 mL) were placed in a round bottom flask and refluxed overnight. To the reaction mixture were then added ethyl acetate (100 mL) and water (100 mL) and the resulting mixture stirred for 30 minutes. The organic layer was separated and dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield a crude solid. The crude solid was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate] to yield the title compound as a residue.

Workup

  1. temperaturerefluxed overnight
  2. customThe organic layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto yield a crude solid
  7. customThe crude solid was purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate]

Sources & evidence

ORD record
ord-1c5d99f2cc2d4519bef9afd009cec41f
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530475B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes