Potassium Fluoride → 4-(4-Chloro-2-methylphenyl)-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

HRID 1472772ノート

反応式

HRID 1472772 の反応式
Br[C:2]1[CH:3]=[C:4]([C:18]#[N:19])[S:5][C:6]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[CH:9][CH:8]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[C:23]([CH3:30])[CH:22]=1.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[C:4]([C:18]#[N:19])[S:5][C:6]=2[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[CH:9][CH:8]=2)=[C:23]([CH3:30])[CH:22]=1

参加物

5

反応物 3

HCID 522689Potassium FluorideHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 682936224-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

生成物 1

HCID 682936984-(4-Chloro-2-methylphenyl)-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile収率 90.6%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

A round-bottomed flask was charged with 4-bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile (203 mg, 0.62 mmol), 4-chloro-2-methylphenylboronic acid (119 mg, 0.70 mmol), Pd2(dba)3 (9.2 mg, 0.010 mmol) and KF (126 mg, 2.17). After degassed, dioxane (2.0 mL) and P(Bu-t)3 (0.15 mL, 0.2M, 0.03 mmol) was added. The reaction mixture was stirred at rt until complete. 20 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=3:1). 0.21 g (90.6%) of product was obtained as a white solid.

後処理

  1. customAfter degassed
  2. additiondioxane (2.0 mL) and P(Bu-t)3 (0.15 mL, 0.2M, 0.03 mmol) was added
  3. addition20 mL of water was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane:CH2Cl2=3:1)

出典と根拠

ORDレコード
ord-cad9fe2fa4a04c468171590c5702b5e0
出典データセット
uspto-grants-2015_04
特許番号
US09012655B2

反応ノート

読み込み中…