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1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-Methoxy-4-((5-phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

HRID 219083
Notes
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Reaction equation

HRID 219083 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[N:14][C:15]([C:16]([O-:18])=O)=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([CH2:31][C:32]([O:34][CH3:35])=O)[CH:26]=2)C=CC=CC=1.[CH2:36]1CCN2C(=NCCC2)C[CH2:37]1.C(NC1C=CC(S(N=[N+]=[N-])(=O)=O)=CC=1)(=O)C>CC#N>[CH3:35][O:34][C:32]1[CH:31]=[C:27]2[C:26]([C:25]([O:18][CH2:16][C:15]3[N:14]=[N:13][N:10]4[CH:11]=[CH:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=34)=[CH:30][CH:29]=[N:28]2)=[CH:37][CH:36]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 51291854-Acetamidobenzenesulfonyl azideHCID 67503470Methyl 2-(4-phenylpyridin-2-yl)acetateHCID 866302645-Phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 576913407-Methoxy-4-((5-phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Procedure

5-Phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate. To a solution of methyl 2-(4-phenylpyridin-2-yl)acetate (see Lohse, O.; Thevenin, P.; Waldvogel, E. Synlett 1999, 1, 45-48) (0.504 g, 2.22 mmol) in 12 mL CH3CN was added DBU (0.501 ml, 3.33 mmol) and the mixture cooled in an ice bath. To the solution, 4-acetamidobenzenesulfonyl azide (0.533 g, 2.22 mmol) was added and the mixture allowed to warm to rt. The mixture was stirred at rt for 5 h then evaporated. The residue was diluted with CH2Cl2, washed with water, brine, dried over Na2SO4, and filtered. The title compound was obtained after purification via flash chromatography.

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. customthen evaporated
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-9777b9de91304c46a43ed3a49353da7b
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198448B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes