Cesium carbonate → Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate

HRID 537034Notes

Reaction equation

HRID 537034 reaction equation
[Br:1][C:2]1[O:3][C:4](Br)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]([NH:27][C:23]1[CH:22]=[C:21]([C:4]2[O:3][C:2]([Br:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=2)[CH:26]=[CH:25][N:24]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 49760417N-(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamideHCID 53216927Ethyl 2,5-dibromofuran-3-carboxylate

Product 1

HCID 66748312Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoateYield 14%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2,5-dibromo-3-furoate (0.21 g, 0.722 mmol) in 1,4-dioxane (2.2 mL) and water (0.50 mL) were added tetrakis(triphenylphosphine) palladium(0) (0.08 g, 0.07 mmol), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (0.19 g, 0.72 mmol) and cesium carbonate (0.71 g, 2.2 mmol). The reaction mixture was subjected to microwave irradiation at 95° C. for 15 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate (0.035 g, 14%) as a white solid. LCMS (FA): m/z=339.1 (M+H).

Workup

  1. customirradiation at 95° C. for 15 min
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-15b71ea8d78444dea49ff0abc2951521
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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