Potassium Carbonate → HCID 66779795, compound

HRID 1470384Notes

Reaction equation

HRID 1470384 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9](I)[O:10][C:3]=12.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=2)[NH2:23])O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:20]3[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=3)[NH2:23])[O:10][C:3]=12

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66779473HCID 66779473, compound

Product 1

HCID 66779795HCID 66779795, compoundYield 20.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a 20-mL microwave vial was added 7-chloro-2-iodo-furo[3,2-b]pyridine (500.00 mg; 1.79 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (431.19 mg; 1.97 mmol), palladium(ii) acetate (20.08 mg; 0.09 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (73.45 mg; 0.18 mmol), and potassium carbonate (741.81 mg; 5.37 mmol). The reagents were suspended in dioxane (6.00 ml) and water (0.60 ml) and run in microwave reactor at 150° C. for 2 hours. The reaction mixture was cooled to room temperature, dried over Na2SO4, filtered and concentrated. The crude mixture was purified using Biotage column chromatography (50-100% EtOAc/Hexanes) to afford the title compound as a yellow solid (88.20 mg, 20%).

Workup

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude mixture was purified

Sources & evidence

ORD record
ord-afd6721af5b54e1291ec14f88aab85ab
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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