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Triphenylphosphine → 6-bromo-2-(2-(quinolin-2-yl)ethyl)-[1,2,4]-triazolo[4,3-a]pyridin-3(2H)-one

HRID 1777781
Notes
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Reaction equation

HRID 1777781 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:47][C:48]1[CH:49]=[CH:50][C:51]2[N:52]([C:54](=[O:57])[NH:55][N:56]=2)[CH:53]=1>C1COCC1>[Br:47][C:48]1[CH:49]=[CH:50][C:51]2[N:52]([C:54](=[O:57])[N:55]([CH2:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[N:56]=2)[CH:53]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 120407986-bromo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

Product 1

HCID 715733846-bromo-2-(2-(quinolin-2-yl)ethyl)-[1,2,4]-triazolo[4,3-a]pyridin-3(2H)-oneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 1-dram vial were placed 2-(quinolin-2-yl)ethanol (405 mg, 2.80 mmol), DIAD (472 mg, 2.34 mmol) and triphenylphosphine (613 mg, 2.34 mmol) in THF (11.7 mL). The mixture was stirred at room temperature for 10 min, and 3-3 (600 mg, 2.80 mmol) was added in one portion. The reaction was further stirred for 10 min. The crude product was dried under stream of N2 and purified by reversed phase HPLC to give 480 mg (55%) of 3-4. HRMS (ES) 369.0348 (M+H) found, 369.0349 required.

Workup

  1. stirringThe reaction was further stirred for 10 min
  2. dry with materialThe crude product was dried under stream of N2
  3. custompurified by reversed phase HPLC

Sources & evidence

ORD record
ord-e38ff1c358854b089118250bc457bd8b
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266881B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes