1-(diphenylmethyl)-1H-indole-2,3-dione → HCID 67357402, 화합물

HRID 1965327노트

반응식

HRID 1965327 반응식
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([Mg]Cl)(C)C.[C:16]1([CH:22]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[C:24]2=[O:33])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.ClCCl>[C:34]1([CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:5]3[CH:6]=[C:7]([O:8][CH3:9])[C:2]([F:1])=[CH:3][C:4]=3[OH:10])([OH:32])[C:24]2=[O:33])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

참가 물질

6

반응물 3

HCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 146616133-Fluoro-4-methoxyphenolHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 67357402HCID 67357402, 화합물수율 57%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-fluoro-4-methoxyphenol (Niemann, M. B. J. Am. Chem. Soc. (1941), 63:609) (4.60 g, 32.4 mmol) in tetrahydrofuran (60 mL) at 5° C. was added a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (18.0 mL, 36.0 mmol). Tetrahydrofuran was removed under reduced pressure and dichloromethane (60 mL) was added. To the solution was added a solution of 1-(diphenylmethyl)-1H-indole-2,3-dione (8.00 g, 25.5 mmol) in dichloromethane (60 mL) at 5° C. and the reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with saturated ammonium chloride solution (5 mL). The reaction mixture was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was subjected to column chromatography with 40% to 90% gradient of ethyl acetate in hexanes to afford 1-(diphenylmethyl)-3-(4-fluoro-2-hydroxy-5-methoxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (6.60 g, 57%) as a pink solid: MS (ES+) m/z 438.3 (M−17).

후처리

  1. customTetrahydrofuran was removed under reduced pressure and dichloromethane (60 mL)
  2. additionwas added
  3. customThe reaction mixture was quenched with saturated ammonium chloride solution (5 mL)
  4. dry with materialThe reaction mixture was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-044651c051f844e388562536e2e9f47a
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415370B2

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