Sodium Methoxide → HCID 118006166, compound

HRID 926453Notes

Reaction equation

HRID 926453 reaction equation
Cl[C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[C:10]([Cl:23])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:24])[CH:8]=2)[N:3]=1.[CH3:25][O-:26].[Na+]>C1(C)C=CC=CC=1>[Cl:23][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:24])[CH:8]=2)[N:3]=[C:2]([O:26][CH3:25])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 118006107HCID 118006107, compound2×

Product 1

HCID 118006166HCID 118006166, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2,4-dichloro-6-iodo-3-(3-(trifluoromethyl)benzyl)quinoline (1.551 g, 3.217 mmol, Intermediate 7: step b) and sodium methoxide (1.738 g, 32.174 mmol) in dry toluene (16 mL) was heated at 90° C. for 16 hours. The reaction was cooled to room temperature and quenched by the addition of saturated aqueous NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified (FCC, 80 g SiO2, 0-20% CH2Cl2/hexanes over 20 minutes) to afford the title compound.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by the addition of saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified (FCC, 80 g SiO2, 0-20% CH2Cl2/hexanes over 20 minutes)

Sources & evidence

ORD record
ord-10d8e997efed4f94ad2283d820ae556e
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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