Potassium Carbonate → HCID 86686286, compound

HRID 2172598Notes

Reaction equation

HRID 2172598 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][CH2:20][C:21]3[CH:26]=[CH:25][C:24](OC)=[CH:23][CH:22]=3)[N:13]=[C:12]2[CH3:29])[CH:5]=1.[F:31]C1C=CC(CBr)=CC=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][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:31])=[CH:23][CH:22]=3)[N:13]=[C:12]2[CH3:29])[CH:5]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 680214-Fluorobenzyl bromideHCID 86686287HCID 86686287, compound

Product 1

HCID 86686286HCID 86686286, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 3 (120 mg, 0.39 mmol) in N,N-dimethylformamide (2 mL) was added 4-fluorobenzyl bromide (0.05 mL, 0.39 mmol), potassium carbonate (81 mg, 0.58 mmol) and 18-crown-6 (10 mg). The slurry was stirred at ambient temperature for two hours. 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 colorless oil. (63 mg, 38% yield). MS (M+H): 417

Workup

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

Sources & evidence

ORD record
ord-78bc2b22c7dc4123aaa8e785412c92bb
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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