Diisopropylamine → Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate

HRID 558244노트

반응식

HRID 558244 반응식
Br[C:2]1[C:3]([F:21])=[C:4]([F:20])[C:5]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N(C(C)C)C(C)C.[Si:29]([C:33]#[CH:34])([CH3:32])([CH3:31])[CH3:30]>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:5]1[C:4]([F:20])=[C:3]([F:21])[C:2]([C:34]#[C:33][Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

7

반응물 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

생성물 1

HCID 59519400Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate수율 85.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To an oven dried flask charged with a solution of methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate (21.68 mmol, 8.1 g) in THF (116 ml), was added CuI (2.16 mmol, 0.4 g) and iPr2NH (43.36 mmol, 6.1 ml). After addition is completed, reaction was purged with Argon and Pd(PPh3)2Cl2 (3.73 mmol, 2.62 g) and TMS-acetylene (26.88 mmol, 3.7 ml) are added. The reaction mixture was stirred at room temperature for 16 h, concentrated and taken up in EtOAc. The organic fraction was washed with sat NH4Cl, brine, dried over MgSO4 and conc. The crude was purified by flash chromatography using 5% to 20% EtOAc in Hexane to afford the desired product 6.96 g (85%).

후처리

  1. customTo an oven dried flask
  2. additionAfter addition
  3. customreaction
  4. additionare added
  5. concentrationconcentrated
  6. washThe organic fraction was washed with sat NH4Cl, brine
  7. dry with materialdried over MgSO4
  8. customconc. The crude was purified by flash chromatography

출처 및 근거

ORD 기록
ord-38d7f5ff75a74078a3ceb1ab52de9449
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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