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1-Fluoro-2-iodo-4-(methylsulfonyl)benzene → Tert-butyl(4-cyano-2-{[2-fluoro-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390166
ノート
印刷プレビュー

反応式

HRID 2390166 の反応式
[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[CH:18])([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][C:22]=1I>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[C:18][C:22]1[CH:23]=[C:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=[CH:26][C:21]=1[F:20])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 585218581-Fluoro-2-iodo-4-(methylsulfonyl)benzene2 回HCID 58522073Tert-butyl(4-cyano-2-ethynylphenoxy)acetate2 回

生成物 1

HCID 58521827Tert-butyl(4-cyano-2-{[2-fluoro-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate収率 78%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
70 °C

実験手順

A suspension of (4-cyano-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 46; 200 mg; 0.78 mmol), 1-fluoro-2-iodo-4-(methylsulfonyl)benzene (Intermediate 77; 233 mg; 0.78 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) (34 mg; 0.05 mmol) and cuprous iodide (9 mg; 0.05 mmol) was degassed during 2 minutes under nitrogen then anhydrous THF (3 ml) and TEA (215 μl; 1.55 mmol) were added and the reaction mixture was stirred at 70° C. for 16 hours. The solvents were removed under reduced pressure and the residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound (260 mg, 78%) as a yellow sticky solid.

後処理

  1. customwas degassed during 2 minutes under nitrogen
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was purified by flash column chromatography (silica)
  4. washeluting with cyclohexane containing
  5. temperatureincreasing amounts of EtOAc

出典と根拠

ORDレコード
ord-aef323e15f7d4082a9a9aaa18fcadc05
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273769B2

反応ノート

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