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Potassium Carbonate → HCID 86699303, compound

HRID 2199519
Notes
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Reaction equation

HRID 2199519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]2=[O:16])[C:5]([CH3:17])=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCCC>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)=[CH:10][C:9]2=[O:16])[C:5]([CH3:17])=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 21899848Ethylacetate heptaneHCID 86343533HCID 86343533, compound

Product 1

HCID 86699303HCID 86699303, compound

Reagents, catalysts & solvents 2

HCID 28557
18-Crown-6
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′-chloro-4-hydroxy-6,5′-dimethyl-[1,4′]bipyridinyl-2-one of part A (1.5 g, 6.0 mmol) in N,N-dimethylformamide (10 mL) was added 4-methoxybenzylbromide (1.33 g, 6.6 mmol), potassium carbonate (2.1 g, 15.1 mmol) and 18-crown-6 (40 mg). The slurry was stirred at ambient temperature for 18 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 solution was concentrated in vacuo to provide a brown oil. Normal phase chromatography (ethyl acetate/heptane) provided the alkylated product (1.37 g): MS (M+H) 372.

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. concentrationThe solution was concentrated in vacuo
  5. customto provide a brown oil

Sources & evidence

ORD record
ord-152c5fc8bde8439b94e4aaaa81359b0b
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359300B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes