Pyridine → HCID 59774860, compound

HRID 2422528Notes

Reaction equation

HRID 2422528 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:40]1C=CC=CC=1.[N:46](C(OC(C)C)=O)=[N:47]C(OC(C)C)=O>C1(C)C=CC=CC=1.[Zn](N=[N+]=[N-])N=[N+]=[N-]>[N:40]([CH2:1][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1)=[N+:46]=[N-:47]

Participants

7

Reactant 4

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57437845HCID 57437845, compound

Product 1

HCID 59774860HCID 59774860, compound

Reagents, catalysts & solvents 2

HCID 178514646Zinc azideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 7-formyl-4-phenylquinoline-2-carbonitrile (520 mg, 2.0 mmol) in toluene (12 mL) was added triphenylphosphine (1.05 g, 4.0 mmol), Zn(N3)2.2 pyridine (461 mg, 1.5 mmol) and diisopropyl azodicarboxylate (787 μL, 4.0 mmol). The mixture was stirred at room temperature for 3 h, concentrated and purified on silica gel (eluting with EtOAc/hexanes, 3:7) to give the title compound. MS (+ESI): 286 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified on silica gel (eluting with EtOAc/hexanes, 3:7)

Sources & evidence

ORD record
ord-72e34ae5440f4cb79bb8595cbda265bb
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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