Sodium Carbonate → HCID 86723271、化合物

HRID 1846050ノート

反応式

HRID 1846050 の反応式
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([F:21])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25](I)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([F:29])=[C:27]([C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[F:21])[CH:28]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27736524-Chloro-1-fluoro-2-iodobenzeneHCID 86723254HCID 86723254、化合物

生成物 1

HCID 86723271HCID 86723271、化合物収率 28%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-(4-(ethylsulfonyl)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 45, 1.77 g, 5.64 mmol), 4-chloro-1-fluoro-2-iodobenzene (1.28 g, 5.00 mmol), and sodium carbonate (1.59 g, 15.00 mmol) in dioxane (40 mL) and water (10 mL) was degassed. Tetrakis(triphenylphosphine)palladium(0) (577 mg, 0.50 mmol) was added and the mixture was degassed twice more, and the reaction warmed to 80° C. for 2 hours. The reaction was cooled and diluted with EtOAc (50 mL) and water (50 mL), the layers separated and the aqueous extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4 and the solvent removed in vacuo. The crude was purified by silica gel column chromatography eluting with EtOAc:heptane 1:19 to 1:1 to give the title compound as a colourless oil 28% yield, 443 mg.

後処理

  1. customthe mixture was degassed twice more
  2. temperatureThe reaction was cooled
  3. additiondiluted with EtOAc (50 mL) and water (50 mL)
  4. customthe layers separated
  5. extractionthe aqueous extracted with EtOAc (2×30 mL)
  6. washThe combined organic layers were washed with brine (30 mL)
  7. dry with materialdried over MgSO4
  8. customthe solvent removed in vacuo
  9. customThe crude was purified by silica gel column chromatography
  10. washeluting with EtOAc:heptane 1:19 to 1:1

出典と根拠

ORDレコード
ord-0e80d6acb98e43b5ba37d15383f7a503
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

反応ノート

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