1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58081364, compound

HRID 928434Notes

Reaction equation

HRID 928434 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12]O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.C1C=CC(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.[Cl-].[Na+].O>[N:39]([CH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([CH3:1])[CH:11]=2)=[N+:40]=[N-:41]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 58081223HCID 58081223, compound

Product 1

HCID 58081364HCID 58081364, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (7-methylquinolin-3-yl)methanol 41.5 mg, 0.232 mmol) and DBU (0.063 ml, 0.418 mmol) in DMF (0.8 ml) was added DPPA (0.085 ml, 0.395 mmol). The reaction mixture was stirred for 1.5 h at 23° C. Reaction mixture was poured in brine and extracted twice with ethyl acetate. Organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound. HPLC (Method G) Rt=1.174 min, MS (Method V) [M+H]+=199.2.

Workup

  1. customReaction mixture
  2. extractionextracted twice with ethyl acetate
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b1a0423688b54ee9bcbe7652ba019bf1
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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