Potassium Hydroxide → 5-(Difluoromethoxy)-4-iodo-2-methoxypyridine

HRID 56855

반응식

HRID 56855 반응식
[OH-].[K+].[I:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[CH:6][C:5]=1[OH:12].[F:13][C:14](F)([F:22])S(OC(F)F)(=O)=O>C(#N)C.O>[F:13][CH:14]([F:22])[O:12][C:5]1[C:4]([I:3])=[CH:9][C:8]([O:10][CH3:11])=[N:7][CH:6]=1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 542802Difluoromethyl trifluoromethanesulfonateHCID 120277864-Iodo-6-methoxypyridin-3-ol

생성물 1

HCID 1176053175-(Difluoromethoxy)-4-iodo-2-methoxypyridine

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

4.8 ml of aqueous potassium hydroxide solution (6M) were added to a solution of 600 mg (purity 93%, 2.22 mmol) of 4-iodo-6-methoxypyridin-3-ol in 4.8 ml of acetonitrile, the mixture was cooled in an ice bath and 863 μl (purity 75%, 3.56 mmol, 1.6 eq.) of difluoromethyl trifluoromethanesulphonate [Angew. Chem. Int. Ed. 2013, 52, 1-5; Journal of Fluorine Chemistry 2009, 130, 667-670] were added with vigorous stirring. The reaction mixture was stirred for 2 min and diluted with 33 ml of water. The aqueous phase was extracted twice with in each case 40 ml of diethyl ether. The combined organic phases were dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. The crude product was purified by flash chromatography (IR-50SI, petroleum ether/ethyl acetate 12-20%). Yield: 407 mg (purity 90%, 55% of theory)

후처리

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionThe aqueous phase was extracted twice with in each case 40 ml of diethyl ether
  3. dry with materialThe combined organic phases were dried (sodium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried
  7. customThe crude product was purified by flash chromatography (IR-50SI, petroleum ether/ethyl acetate 12-20%)

출처 및 근거

ORD 기록
ord-fcb6b0de660543c1a3e2b855c42f019b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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