Sodium Methoxide → HCID 118005574, compound

HRID 1478491Notes

Reaction equation

HRID 1478491 reaction equation
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][C:15]([C:20]([C:32]1[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=1)([C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1)[OH:21])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][O-:40].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:10]([O:40][CH3:39])=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][C:15]([C:20]([C:32]1[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=1)([C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=1)[OH:21])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 118005572HCID 118005572, compound2×

Product 1

HCID 118005574HCID 118005574, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of (3-(benzyloxy)-2,4-dichloroquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol (2.46 g, 4.4 mmol, Intermediate 11: step d) in methanol (24.6 mL) was added NaOMe (0.5 M in MeOH, 8.8 mL, 4.4 mmol) and the resulting suspension heated to 65° C. for 8 hours. The mixture was then cooled to room temperature and concentrated to dryness. Water was added and the mixture acidified with 2 N aqueous HCl to ˜pH 2. The aqueous was then extracted with EtOAc. The organics were combined and washed with water, saturated aqueous NaHCO3 and brine. The organics were then dried (MgSO4), filtered and concentrated to dryness to afford the title compound which was used without further purification.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated to dryness
  3. additionWater was added
  4. extractionThe aqueous was then extracted with EtOAc
  5. washwashed with water, saturated aqueous NaHCO3 and brine
  6. dry with materialThe organics were then dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-556daf1a258c48288a42599a08718c83
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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