2-Fluoro-4-iodoaniline → 3,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

HRID 558186노트

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HRID 558186 반응식
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:21]1[C:29]([F:30])=[C:28]([F:31])[C:27]([N+:32]([O-:34])=[O:33])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]>C1COCC1>[F:30][C:29]1[C:21]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:2]=2[F:1])=[C:22]([CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[C:28]=1[F:31])[C:23]([OH:25])=[O:24]

참가 물질

5

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HCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium Hexamethyldisilazide2회HCID 158712412,3,4-Trifluoro-5-nitrobenzoic acid

생성물 1

HCID 210742923,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

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온도
-78 °C

실험 절차

To a solution of 2-fluoro-4-iodoaniline (2.9 g, 11.8 mmoles) in 50 ml anhydrous THF at −60° C., 40 ml of a 1M solution of LHMDS in THF (40 mmoles) is added dropwise. In a separate flask, 2,3,4-trifluoro-5-nitrobenzoic acid (5 g, 22.6 mmoles), previously dissolved in THF (50 ml), is treated, at −60° C., with 25 ml of a 1M solution of LHMDS in THF (25 mmoles). Both solutions are stirred at −78° C. for 45 min and the second solution is transferred via cannula to the first reaction mixture. After completion of the addition the resulting mixture is stirred under argon at room temperature for 15 hours. The reaction mixture is quenched with water, then 1N HCl is added (pH=0-1) followed by brine (100 ml). The crude material is extracted with THF (3×100 ml), the organic layers are combined and dried (Na2SO4) and the solvent is removed to give the title compound.

후처리

  1. additionAfter completion of the addition the resulting mixture
  2. stirringis stirred under argon at room temperature for 15 hours
  3. customThe reaction mixture is quenched with water
  4. addition1N HCl is added (pH=0-1)
  5. extractionThe crude material is extracted with THF (3×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent is removed

출처 및 근거

ORD 기록
ord-71122d5eeacc43faae9109f1c7438aed
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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