Toluene → 7-Fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17313노트

반응식

HRID 17313 반응식
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.[CH3:20][O:21][CH2:22][C:23]([O:25][C:26]1[C:27]([F:42])=[C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:29]([CH3:35])=[C:30]([C:33]#[N:34])[C:31]=1[NH2:32])=O>C(OCC)(=O)C>[F:42][C:27]1[C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:29]([CH3:35])[C:30]([C:33]#[N:34])=[C:31]2[C:26]=1[O:25][C:23]([CH2:22][O:21][CH3:20])=[N:32]2

참가 물질

5

반응물 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 866308254-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl methoxyacetate

생성물 1

HCID 685851157-Fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 79.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

p-Toluenesulfonic acid monohydrate (38 mg, 0.2 mmol) was added to a toluene (30 ml) solution of 4-amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl methoxyacetate (I-58) (214 mg, 0.68 mmol), followed by stirring for 3 hours and a half with heating under reflux. After cooling to room temperature, the reaction liquid was diluted with ethyl acetate, washed with saturated sodium bicarbonate water and saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure to obtain the entitled compound (160 mg, 79%) as a pale yellow solid.

후처리

  1. temperaturea half with heating
  2. temperatureunder reflux
  3. customthe reaction liquid
  4. washwashed with saturated sodium bicarbonate water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration under reduced pressure
  7. concentrationthe eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-433faaa8360747c4866bfea78d305049
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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