Water → HCID 66666781, compound

HRID 1620351Notes

Reaction equation

HRID 1620351 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1F)[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:11][C:4]1[CH:5]=[N:6][C:7]([CH:8]2[CH2:9][CH2:10]2)=[C:2]([Cl:1])[CH:3]=1)[C:16]#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1235793-Bromo-4-fluorobenzonitrileHCID 580424875-Chloro-6-cyclopropylpyridin-3-OL

Product 1

HCID 66666781HCID 66666781, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

5-chloro-6-cyclopropylpyridin-3-ol (250 mg, 1.47 mmol), 3-bromo-4-fluorobenzonitrile (Preparation 37, 295 mg, 1.47 mmol) and potassium carbonate (611 mg, 4.42 mmol) were suspended in dimethylsulfoxide (6 mL). The reaction mixture was stirred at 5 hours at 50° C. then water (60 mL) was added and the suspension was extracted by ethyl acetate (3×30 mL). The organic layers were combined, washed with brine (3×15 mL), dried over magnesium sulfate, filtered and concentrated under vacuum to afford the title compound as a clear oil which solidified on standing (485 mg, 94%).

Workup

  1. extractionthe suspension was extracted by ethyl acetate (3×30 mL)
  2. washwashed with brine (3×15 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6699efd91eca4fa188687f5f7f217aa3
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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