Isopropanol → HCID 50953576, compound

HRID 1035055Notes

Reaction equation

HRID 1035055 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(O)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 810792-ChloronicotinonitrileHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 50953576HCID 50953576, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a 250-mL, round-bottomed flask containing a large magnetic stir bar were added 2-chloro-3-cyanopyridine (1.39 g, 10.0 mmol), 2-methoxyphenylboronic acid (1.82 g, 12.0 mmol), and dichlorobis(triphenylphosphine)palladium(II) (351 mg, 0.50 mmol). Isopropyl alcohol (50 mL) and 2M sodium carbonate solution (50 mL) were added. The flask was stoppered and immersed in an oil bath heated to 80-90° C. The biphasic mixture was stirred vigorously and heated for 8 hours. After cooling to room temperature, ethyl acetate (50 mL) was added and the black mixture was transferred to a separatory funnel. The aqueous layer was removed and subsequently extracted with ethyl acetate (3×20 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator to give a brown oil. The product was crystallized from ethyl acetate/hexanes to give 1.38 g (66%) of the title compound as a tan powder.

Workup

  1. additionTo a 250-mL, round-bottomed flask containing a large magnetic stir bar
  2. customimmersed in an oil bath
  3. temperatureheated for 8 hours
  4. temperatureAfter cooling to room temperature
  5. customthe black mixture was transferred to a separatory funnel
  6. customThe aqueous layer was removed
  7. extractionsubsequently extracted with ethyl acetate (3×20 mL)
  8. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporator
  11. customto give a brown oil
  12. customThe product was crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-33b3d71a8b664a698e7a8a46d5b24690
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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