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Triphenylphosphine → 7-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one

HRID 920936
Notes
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Reaction equation

HRID 920936 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:34][C:35]1[C:36]2[O:44][CH:43]=[CH:42][C:37]=2[C:38](=[O:41])[NH:39][CH:40]=1.[N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47][C:46]=1[CH2:55][CH2:56]O>C1COCC1>[Br:34][C:35]1[C:36]2[O:44][CH:43]=[CH:42][C:37]=2[C:38](=[O:41])[N:39]([CH2:56][CH2:55][C:46]2[CH:47]=[CH:48][C:49]3[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:45]=2)[CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 179855277-Bromofuro[3,2-c]pyridin-4(5H)-one

Product 1

HCID 866831507-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-oneYield 23%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

DIAD (4.91 mmol, 992 mg) was added dropwise to PPh3 (753 mg, 2.80 mmol) in 20 mL of THF. The mixture was stirred for 30 min. Then 7-bromofuro[3,2-c]pyridine-4(5H)-one (300 mg, 1.402 mmol) was added followed by the addition of 2-(quinolin-2-yl)ethanol (243 mg, 1.402 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was extracted with water/ethyl acetate. The organic phase was extracted with 1N HCl. The acidic aqueous phase was basified with 1N NaOH and extracted with DCM. The organic phase was extracted with water, dried over MgSO4, filtered, concentrated and purified by chromatography to give the title compound as white solid (119 mg, 23%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water/ethyl acetate
  3. extractionThe organic phase was extracted with 1N HCl
  4. extractionextracted with DCM
  5. extractionThe organic phase was extracted with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by chromatography

Sources & evidence

ORD record
ord-f119be6a656d4192b77628b678fac095
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273068B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes