Potassium Carbonate → HCID 66666696, compound

HRID 1620319Notes

Reaction equation

HRID 1620319 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[C:14](B(O)O)=[CH:13][CH:12]=[CH:11][N:10]=1.Br[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[O:35][CH3:36])[C:22]#[N:23]>O1CCOCC1.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>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([O:27][C:26]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=2[C:14]2[C:9]([O:8][CH3:7])=[N:10][CH:11]=[CH:12][CH:13]=2)=[C:29]([O:35][CH3:36])[CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acid2×HCID 66667179HCID 66667179, compound

Product 1

HCID 66666696HCID 66666696, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (0.232 g, 1.68 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.215 g, 1.26 mmol) were added to a solution of 3-bromo-4-(4-chloro-2-methoxyphenoxy)benzonitrile (Preparation 3, 0.284, 0.839 mmol) in dioxane (10 mL). The reaction was degassed three times, then tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) was added and the mixture was degassed three further times. The resulting mixture was heated at 70° C. over for 72 hours, then the reaction was cooled to room temperature. Then (2-methoxypyridin-3-yl)boronic acid (0.072 g, 0.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) were added and the reaction was heated at 90° C. for 3 hours. The reaction was allowed to cool to room temperature and the solvent removed in vacuo to give a black oil which was absorbed onto silica and purified by silica gel chromatography (Biotage®, SNAP cartridge 50 g, DCM 6CV then 99/1, DCM/MeOH 5 CV and then 9/1, DCM/MeOH 6 CV) to afford the title compound as a white solid (0.265 g).

Workup

  1. customThe reaction was degassed three times
  2. customthe mixture was degassed three further times
  3. temperaturethe reaction was cooled to room temperature
  4. temperaturethe reaction was heated at 90° C. for 3 hours
  5. temperatureto cool to room temperature
  6. customthe solvent removed in vacuo
  7. customto give a black oil which
  8. customwas absorbed onto silica
  9. custompurified by silica gel chromatography (Biotage®, SNAP cartridge 50 g, DCM 6CV then 99/1, DCM/MeOH 5 CV

Sources & evidence

ORD record
ord-1c4651963cf143d1915dc4bab2a90460
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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