Potassium Carbonate → HCID 68048523, compound

HRID 1620321Notes

Reaction equation

HRID 1620321 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:29]=[N:30][C:31]([O:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[CH:32][CH:33]=1)[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>[CH2:35]([O:34][C:31]1[N:30]=[CH:29][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)=[CH:33][CH:32]=1)[CH:36]([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 66668517HCID 66668517, compound

Product 1

HCID 68048523HCID 68048523, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (0.239 g, 1.73 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.162 g, 0.950 mmol) were added to a solution of 3-bromo-4-[(6-isobutoxypyridin-3-yl)oxy]benzonitrile (Preparation 6, 0.300 g, 0.864 mmol) in dioxane (10 mL). The reaction was degassed three times. Tetrakis(triphenylphosphine)palladium(0) (0.010 g, 0.009 mmol) was added and the mixture was degassed three times more. The mixture was heated at 60° C. for 24 hours, then allowed to cool to room temperature and filtered through arbocel, washing with DCM/MeOH (1/1, 50 mL). The combined filtrates were concentrated in vacuo. The residue was absorbed onto silica and purified by silica gel chromatography (Biotage®, SNAP cartridge 50 g, gradient from 5 to 10% EtOAc in heptane 6, then 10% EtOAc in Heptane) to yield the title compound as a solid (0.257 g).

Workup

  1. customThe reaction was degassed three times
  2. customthe mixture was degassed three times more
  3. temperatureto cool to room temperature
  4. filtrationfiltered through arbocel
  5. washwashing with DCM/MeOH (1/1, 50 mL)
  6. concentrationThe combined filtrates were concentrated in vacuo
  7. customThe residue was absorbed onto silica
  8. custompurified by silica gel chromatography (Biotage®, SNAP cartridge 50 g, gradient from 5 to 10% EtOAc in heptane 6

Sources & evidence

ORD record
ord-016a14387bec49ea8bff59d1c7009b3f
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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