Potassium Carbonate → HCID 58168076, compound

HRID 1029071Notes

Reaction equation

HRID 1029071 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13](C(OCC)=O)=[C:14](B(O)O)[CH:15]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[C:53](=[O:56])([O-])[O-].[K+].[K+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]2[C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[NH:1][C:53](=[O:56])[C:12]=2[CH:11]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 44784921[5-Chloro-2-(ethoxycarbonyl)phenyl]boronic acid

Product 1

HCID 58168076HCID 58168076, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

2-Amino-3-bromopyridine (87 mg, 0.50 mmol), 5-chloro-2-ethoxycarbonylphenylboronic acid (149 mg, 0.65 mmol), palladium(II) acetate (5 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (16 mg, 0.04 mmol), and potassium carbonate (207 mg, 1.50 mmol) were dissolved in dioxane/H2O (1.65 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 5 (29 mg, 25% yield) as a solid. LC-MS (M+H=231, obsd.=231). 1H NMR (400 MHz, d6-DMSO): δ 12.18 (s, 1H), 8.91 (dd, 1H), 8.68 (d, 1H), 8.54 (dd, 1H), 8.32 (d, 1H), 7.74 (dd, 1H), 7.34 (dd, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. washThe precipitate was washed with EtOAc/H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b8664fd3977849768ee9c8824101fe13
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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