Trifluoroacetic acid → 6-chloro-4'-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504452

반응식

HRID 504452 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH:8]=[N:9][C:10]([O:12][Si](C)(C)C)=[CH2:11])[CH:7]=1.C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([Cl:34])[CH:32]=2)[C:27](=[CH:35][C:36]2[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=2[O:43][C:44]2([C:48]([O:50][CH3:51])=[O:49])[CH2:47][CH2:46][CH2:45]2)[C:26]1=[O:52])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[Cl:34][C:31]1[CH:32]=[C:33]2[NH:25][C:26](=[O:52])[C:27]3([CH:35]([C:36]4[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=4[O:43][C:44]4([C:48]([O:50][CH3:51])=[O:49])[CH2:45][CH2:46][CH2:47]4)[CH2:12][C:10](=[O:11])[NH:9][CH:8]3[C:6]3[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:17])[C:28]2=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 57565913HCID 57565913, 화합물HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

생성물 1

HCID 765679126-chloro-4'-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
80 °C

실험 절차

To a toluene solution of 1-(5-fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene in toluene (2 M, 5 mL, 10 mmol) was added E/Z 6-chloro-3-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1.5 g, 2.9 mmol). The reaction mixture was heated at 80° C. overnight under argon protection, then TFA (5 mL) was added, and the resulting mixture was stirred at room temperature for 20 min, evaporated in vacuo. The residue was partitioned between ethyl acetate and NaOH aq. (1 M). The organic layer was washed with water, dried over anhydrous Na2SO4, concentrated and purified by column chromatography to give the title compound as a white solid (340 mg).

후처리

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and NaOH aq. (1 M)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-57e54d8bf91d4e21979cdfb6b4e795c9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776875B2

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