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Cesium carbonate → 5-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acid

HRID 537035
Notes
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Reaction equation

HRID 537035 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14](Br)=[C:13]([C:17]([O:19]CC)=[O:18])[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[OH-].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[Cl:22])=[C:13]([C:17]([OH:19])=[O:18])[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 27343222-Chlorophenylboronic acidHCID 66748312Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate

Product 1

HCID 667483155-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acidYield 50%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent2×
HCID 14798Sodium HydroxideSolvent
HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate (0.030 g, 0.09 mmol) in 1,4-dioxane (0.5 mL) and water (0.1 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.010 g, 0.0088 mmol), (2-chlorophenyl)boronic acid (0.018 g, 0.11 mmol), and cesium carbonate (0.087 g, 0.27 mmol). The reaction mixture was subjected to microwave irradiation at 130° C. for 20 min. The reaction mixture was then diluted with water (2 mL) and 1N aqueous sodium hydroxide (0.25 mL) was added. The mixture was allowed to stir at rt overnight. The reaction mixture was extracted with EtOAc and the organic solutions were combined and concentrated. The residue was purified by column chromatography to give 5-[2-(acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acid (0.015 g, 50%) as a white solid. LCMS (FA): m/z=357.4 (M+H).

Workup

  1. customirradiation at 130° C. for 20 min
  2. additionwas added
  3. extractionThe reaction mixture was extracted with EtOAc
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8fa2868fe98d49e692969641acc58991
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes