Trimethylsilyldiazomethane → Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

HRID 558195노트

반응식

HRID 558195 반응식
[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:21][Si](C=[N+]=[N-])(C)C>C1COCC1.CO>[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:21])=[O:8]

참가 물질

5

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 595193885-Bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoic acid

생성물 1

HCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate수율 91%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoic acid (3.0 g, 8.67 mmol) in a mixture of THF (15 ml) and MeOH (5 ml) was added (trimethylsilyl)diazomethane (5.63 ml, 2 M in Hexanes, 11.3 ml). After stirring for 4 h, the reaction was quenched with AcOH and diluted with EtOAc (100 ml). The organic solution was washed with H2O (50 ml) and brine (50 ml), dried over Na2SO4 and concentrated to dryness to give 2.83 g (91%) of methyl 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoate as a light yellow solid.

후처리

  1. customthe reaction was quenched with AcOH
  2. additiondiluted with EtOAc (100 ml)
  3. washThe organic solution was washed with H2O (50 ml) and brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-a771bacddd864080a4671641cb33ef8c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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