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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86703296, compound

HRID 2409982
Notes
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Reaction equation

HRID 2409982 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.[Br:18][C:19]1[N:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][CH:20]=1.C1CCN2C(=NCCC2)CC1>ClCCl>[Br:18][C:19]1[N:24]=[C:23]([CH:25]([C:7]2[C:6]3[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:9][C:8]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[OH:26])[CH:22]=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27570096-Bromopyridine-2-carbaldehydeHCID 107515716-methoxy-2-phenyl-1H-indole

Product 1

HCID 86703296HCID 86703296, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-methoxy-2-phenyl-1H-indole (893 mg) and 6-bromopyridine-2-carboaldehyde (744 mg) in dichloromethane (13.3 mL) was added 1,8-diazabicyclo[5,4,0]-7-undecene (0.060 mL), and the mixture was stirred at room temperature for 13 hours under an argon atmosphere. The reaction mixture was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.43 g). 1H-NMR (CDCl3) δ ppm: 3.81 (3H, s), 4.71 (1H, d, J=2.6 Hz), 6.09 (1H, d, J=2.6 Hz), 6.65 (1H, dd, J=2.3, 8.7 Hz), 6.86 (1H, d, J=2.3 Hz), 7.02-7.13 (2H, m), 7.33-7.54 (5H, m), 7.64-7.72 (2H, m), 8.10 (1H, br s).

Workup

  1. customThe reaction mixture was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4d192f37bb56421982ce9a9a54c9813a
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815903B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes