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Potassium Carbonate → HCID 86686301, compound

HRID 2172633
Notes
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Reaction equation

HRID 2172633 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[C:15]([Cl:18])=[C:14]([O:19]CC3C=CC(OC)=CC=3)[N:13]=[C:12]2[CH3:29])[CH:5]=1.Cl[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[N:34]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[C:15]([Cl:18])=[C:14]([O:19][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[N:34]=3)[N:13]=[C:12]2[CH3:29])[CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 224820332-(Chloromethyl)-6-fluoropyridineHCID 86686287HCID 86686287, compound

Product 1

HCID 86686301HCID 86686301, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of Intermediate 3 (250 mg, 0.81 mmol) in N,N-dimethylformamide (3 mL) was added 2-chloromethyl-6-fluoro-pyridine from Step A (118 mg, 0.81 mmol), potassium carbonate (224 mg, 1.62 mmol) and 18-crown-6 (40 mg). The slurry was heated at 45° C. for eighteen hours. After cooling the reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the alkylated product as a white solid. (180 mg, 53% yield). MS (M+H): 418

Workup

  1. temperatureAfter cooling the reaction
  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 slurry was filtered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-9e0323c27ffc440588b616702833d920
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056110B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes