Water → HCID 58081368, compound

HRID 928430Notes

Reaction equation

HRID 928430 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12]O)[CH:8]=2)[N:3]=1.C1CCN2C(=NCCC2)CC1.C1C=CC(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)=CC=1.O>CN(C=O)C>[N:39]([CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)=[N+:40]=[N-:41]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 2795481(2-methylquinolin-6-yl)methanol

Product 1

HCID 58081368HCID 58081368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (2-methyl-6-quinolinyl)methanol (100 mg, 0.560 mmol) and DBU (0.152 ml, 1.008 mmol) in DMF (4 ml) was added DPPA (0.205 ml, 0.952 mmol). The reaction mixture was stirred overnight at 23° C. Reaction mixture was poured into water and extracted twice with ethyl acetate. Organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated to afford a crude material, which was purified by silicagel chromatography (cyclohexane:ethyl acetate from 100:0 to 0:100) to afford the title compound. HPLC (Method G) Rt=1.048 min; MS (Method F) [M+H]+=199.2

Workup

  1. customReaction mixture
  2. extractionextracted twice with ethyl acetate
  3. washOrganic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a crude material, which
  8. customwas purified by silicagel chromatography (cyclohexane:ethyl acetate from 100:0 to 0:100)

Sources & evidence

ORD record
ord-cc263acb19494ef59fc9891a5f69d718
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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