Sodium Bicarbonate → HCID 66666740, compound

HRID 1620335Notes

Reaction equation

HRID 1620335 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]#[N:6].[CH3:17][O:18][C:19]1[C:24](B(O)O)=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.O.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>[CH3:17][O:18][C:19]1[C:24]([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]#[N:6])=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 66667120HCID 66667120, compound

Product 1

HCID 66666740HCID 66666740, compoundYield 108.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-4-phenoxybenzonitrile (Preparation 21, 0.21 g, 0.7 mmol), (2-methoxypyridin-3-yl)boronic acid (0.2 g, 1.1 mmol) and sodium hydrogen carbonate (0.19 g, 2.1 mmol) was suspended in dioxane (10 mL) and water (3 mL). The reaction mixture was degassed for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.050 g, 0.07 mmol) was added and the mixture heated at 100° C. for 1 hour. After the reaction was allowed to cool to room temperature, the reaction was partitioned between EtOAc (50 mL) and water (15 mL). The organic layer was filtered through a pad of celite and the solvent removed in vacuo to provide a crude brown solid. The crude material was purified by silica gel chromatography eluting with 30% EtOAc in Heptane to afford the title compound as a yellow solid (0.23 g).

Workup

  1. customThe reaction mixture was degassed for 10 minutes
  2. temperatureto cool to room temperature
  3. customthe reaction was partitioned between EtOAc (50 mL) and water (15 mL)
  4. filtrationThe organic layer was filtered through a pad of celite
  5. customthe solvent removed in vacuo
  6. customto provide a crude brown solid
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 30% EtOAc in Heptane

Sources & evidence

ORD record
ord-6d154b92a8844e13a25a7cbee6e95383
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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