Sodium Carbonate → HCID 58432603, compound

HRID 1896232Notes

Reaction equation

HRID 1896232 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([O:19][CH3:20])[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=2)=[C:12]([O:19][CH3:20])[CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5818662-Amino-4-chloropyridineHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acid

Product 1

HCID 58432603HCID 58432603, compoundYield 235.6%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Amino-4-chloro-pyridine (5.00 g, 38.9 mmol) and 4-fluoro-2-methoxyphenylboronic acid (9.26 g, 54.4 mmol) were taken in 1,2-dimethoxy ethane (100 ml). An aqueous solution of sodium carbonate (80 ml, 2 M) was added and argon gas was purged for 30 min. Bis-(triphenyl phosphine) palladium (II) chloride (Pd(PPh3)2Cl2) (272 mg, 0.39 mmol) was added to the reaction mixture and again purged with argon gas for 20 min. The reaction mixture was slowly heated to 85° C.-90° C. with stirring and maintained for 8 h. On completion of reaction, the reaction mixture was cooled to room temperature and the insoluble solid residue filtered. The filtrate was concentrated until 1,2-dimethoxy ethane was fully evaporated. Excess iced-water was added to precipitate the product which was filtered, washed with copious amount of water, and dried under vacuo at 60° C. Again this solid crude product was washed with ethyl acetate in petroleum ether (10%) and dried to afford 20 g (88%) of compound I.

Workup

  1. customargon gas was purged for 30 min
  2. customagain purged with argon gas for 20 min
  3. temperatureThe reaction mixture was slowly heated to 85° C.-90° C.
  4. temperaturemaintained for 8 h
  5. customOn completion of reaction
  6. filtrationthe insoluble solid residue filtered
  7. concentrationThe filtrate was concentrated until 1,2-dimethoxy ethane
  8. customwas fully evaporated
  9. additionExcess iced-water was added
  10. customto precipitate the product which
  11. filtrationwas filtered
  12. washwashed with copious amount of water
  13. customdried under vacuo at 60° C
  14. washAgain this solid crude product was washed with ethyl acetate in petroleum ether (10%)
  15. customdried

Sources & evidence

ORD record
ord-fcf939f5b1204ef29803ddf1081000df
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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