p-Toluenesulfonic acid → 1-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

HRID 452026노트

반응식

HRID 452026 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([OH:11])[OH:10])=[CH:4][C:3]=1[F:13].F[C:15]1C=C(C2C=NC3N(C(CC4C=C5C(=CC=4)N=CC=C5)=CN=3)N=2)C=C[C:16]=1C(NC[C@H](O)C)=O.C([O-])([O-])O[CH2:50][CH3:51].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([O:10][CH2:50][CH3:51])[O:11][CH2:15][CH3:16])=[CH:4][C:3]=1[F:13]

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 533743182-fluoro-N-[(2R)-2-hydroxypropyl]-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide2회HCID 53630039EthylorthoformateHCID 575165211-(4-Bromo-3-fluorophenyl)-2,2-dihydroxyethanone

생성물 1

HCID 575165221-(4-Bromo-3-fluorophenyl)-2,2-diethoxyethanone

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-(4-bromo-3-fluorophenyl)-2,2-dihydroxyethanone and 4-bromo-3-fluorophenyl)(oxo)acetaldehyde (crude product from Step 3, 7.0 g, 28 mmol) in toluene (50 mL) was added ethyl orthoformate (12 mL, 70 mmol) and p-toluenesulfonic acid (200 mg, 1 mmol). The reaction mixture was refluxed for 4 h. The reaction mixture was cooled to RT, diluted with ethyl acetate, washed with aqueous sodium bicarbonate, water, brine, and dried over magnesium sulfate. Concentration under reduced pressure gave the desired product which was used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. washwashed with aqueous sodium bicarbonate, water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-099f00c91bb941e4ab42dba41f944f2c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487096B2

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