HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → 2'-Acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5'-methyl-[1,4']bipyridinyl-2-one

HRID 516983
Notes
Print preview

Reaction equation

HRID 516983 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[C:11]2=[O:18])[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:3])[CH3:2].Cl[CH2:21][C:22]1[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=3)=[C:12]([Cl:17])[C:11]2=[O:18])[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 534037442-(Chloromethyl)-3,5-difluoropyridineHCID 1177296262'-Acetyl-3-chloro-4-hydroxy-5'-methyl-[1,4]bipyridinyl-2-one

Product 1

HCID 1177295302'-Acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5'-methyl-[1,4']bipyridinyl-2-one

Reagents, catalysts & solvents 2

HCID 28557
18-Crown-6
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2′-acetyl-3-chloro-4-hydroxy-5′-methyl-[1,4′]bipyridinyl-2-one of part D (500 mg, 1.7 mmol) in N,N-dimethylformamide (3 mL) was added 2-chloromethyl-3,5-difluoro-pyridine (277 mg, 1.7 mmol), potassium carbonate (590 mg, 4.28 mmol) and 18-crown-6 (10 mg) and the reaction was stirred at 60° C. for 4 h. After cooling the solution was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide alkylated product as a yellow solid (397 mg): MS (ES) m/e 420 (M+H).

Workup

  1. temperatureAfter cooling the solution
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-90c3921b347b445b9224ee3d0a6ce4da
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115089B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes