Water → HCID 67168318, compound

HRID 872841Notes

Reaction equation

HRID 872841 reaction equation
Br[C:2]1[O:6][C:5](/[CH:7]=[CH:8]/[NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[Cl:25].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.[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>[Cl:18][C:19]1[CH:20]=[C:21]([C:2]2[O:6][C:5](/[CH:7]=[CH:8]/[NH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[O:11])=[CH:4][CH:3]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343303,4-Dichlorobenzeneboronic acidHCID 67170289HCID 67170289, compound

Product 1

HCID 67168318HCID 67168318, compound

Reagents, catalysts & solvents 2

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

Procedure

Pyridine-2-carboxylic acid [(E)-2-(5-bromofuran-2-yl)vinyl]amide (0.014 g, 0.0477 mmol) was dissolved in 1,4-dioxane (4.2 ml) in a microwave reaction vial. 3,4-Dichlorophenylboronic acid (0.0091 g, 0.0477 mmol), potassium phosphate tribasic (0.020 g, 0.0954 mmol), 0.7 ml of water and tetrakis(triphenylphosphine)-palladium(0) (0.005 g, 0.0047 mmol) were added. After removal of oxygen the reaction mixture was irradiated for 10 min at 160° C. Then water (7 ml) was added. The product was extracted into EtOAc (2×15 ml). The organic phase was washed with water, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography (eluent: heptane-EtOAc 7:3). 1H NMR (400 MHz, CDCl3): 6.26 (1H, d), 6.29 (1H, d), 6.66 (1H, d), 7.45 (1H, distorted d), 7.48-7.52 (2H, m), 7.69-7.76 (2H, m), 7.91 (1H, td), 8.27 (1H, d), 8.61 (1H, dd), 9.88 (1H, d).

Workup

  1. customAfter removal of oxygen the reaction mixture
  2. customwas irradiated for 10 min at 160° C
  3. additionThen water (7 ml) was added
  4. extractionThe product was extracted into EtOAc (2×15 ml)
  5. washThe organic phase was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (eluent: heptane-EtOAc 7:3)

Sources & evidence

ORD record
ord-0db2024a11d94f4785a63731cc41d8c4
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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