2,6-Di-tert-butyl-4-methylphenol → HCID 86699738、化合物

HRID 515169ノート

反応式

HRID 515169 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 86699738HCID 86699738、化合物収率 60%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e982edd4689e4216917dd9d38df770fc
出典データセット
uspto-grants-2015_08
特許番号
US09108936B2

反応ノート

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