2,6-Di-tert-butyl-4-methylphenol → HCID 86699738, 화합물

HRID 515169노트

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HRID 515169 반응식
ClC1C=CC([N:8]([CH3:32])[C:9]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2OS(C(F)(F)F)(=O)=O)=[O:10])=CC=1.C([C:37]1[CH:42]=[C:41](C)[CH:40]=[C:39](C(C)(C)C)[C:38]=1O)(C)(C)C.[Cl-:49].[Li+].C([Sn](CCCC)(CCCC)[C:56]1[CH2:60][CH2:59][CH2:58][CH:57]=1)CCC>O1CCOCC1.O.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>[Cl:49][C:37]1[CH:38]=[CH:39][C:40]([CH2:32][NH:8][C:9](=[O:10])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[C:56]2[CH2:60][CH2:59][CH2:58][CH:57]=2)=[CH:41][CH:42]=1

참가 물질

8

반응물 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 10915290Stannane, tributyl-1-cyclopenten-1-yl-HCID 86699736HCID 86699736, 화합물

생성물 1

HCID 86699738HCID 86699738, 화합물수율 60%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

To a mixture of trifluoro-methanesulfonic acid [2-[(4-chlorophenyl)-methyl-carbamoyl]-3-methyl-5-morpholin-4-yl-phenyl]ester (synthesized according to the method described in section a) of example 12) (1.0 g, 2.03 mmol) in dioxane (50 ml) are added 2,6-di-tert-butyl-4-methylphenol (0.044 g, 0.20 mmol), lithium chloride (0.688 g, 16.3 mmol) and tributyl-1-cyclopenten-1-yl-stannane (1.46 g, 4.06 mmol). The mixture is degassed and flushed with argon for 30 min followed by the addition bis(triphenylphosphine)palladiumchloride (0.17 g, 0.24 mmol). The resulting mixture is heated at 120° C. for 16 h. The reaction mixture is diluted with water (30 ml) and extracted with ethyl acetate (3×50 ml). The organic layer is washed with water (20 ml), saturated potassium fluoride solution (2×20 ml), brine (20 ml) and dried over anhydrous sodium sulfate. Evaporation under vacuum afforded the crude product, which is purified by column chromatography (silica gel-10% KF, 20% ethyl acetate/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-cyclopenten-1-yl-6-methyl-4-morpholin-4-yl-benzamide (0.50 g, 1.22 mmol, 60%).

후처리

  1. customsynthesized
  2. customThe mixture is degassed
  3. customflushed with argon for 30 min
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe organic layer is washed with water (20 ml), saturated potassium fluoride solution (2×20 ml), brine (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation under vacuum
  8. customafforded the crude product, which
  9. customis purified by column chromatography (silica gel-10% KF, 20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-e982edd4689e4216917dd9d38df770fc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108936B2

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