Benzo(B)Thiophene-2-Boronic Acid → 5-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

HRID 10754

反応式

HRID 10754 の反応式
[F-].[K+].I[C:4]1[C:5]([O:14][CH3:15])=[CH:6][C:7]([O:12][CH3:13])=[C:8]([CH:11]=1)[CH:9]=[O:10].[S:16]1[C:20](B(O)O)=[CH:19][C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]1=2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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].O1CCCC1>[S:16]1[C:20]([C:4]2[C:5]([O:14][CH3:15])=[CH:6][C:7]([O:12][CH3:13])=[C:8]([CH:11]=2)[CH:9]=[O:10])=[CH:19][C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]1=2

参加物

7

反応物 4

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 142459555-Iodo-2,4-dimethoxybenzaldehyde2 回

生成物 1

HCID 161159165-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

Ex-123A: Potassium fluoride (0.42 g, 7.2 mmol), 5-iodo-2,4-dimethoxy-benzaldehyde (Ex-123, 1.0 g, 3.42 mmol), 2-benzo[b]thiophene boronic acid (0.67 g, 3.77 mmol), degased tetrahydrofuran (10 mL), tris(dibenzylideneacetone)dipalladium (19 mg, 0.02 mmol), and tri-tert-butylphosphine (100 mg, 0.05 mmol) were sequentially charged into a flask equipped with a condenser and nitrogen inlet adapter. The reaction mixture was heated at 60° C. for one hour under nitrogen. HPLC analysis indicated of 100% conversion of 5-iodo-2,4-dimethoxy-benzaldehyde (Ex-123) to the title compound prepared through another route (Ex-3A).

後処理

  1. additionwere sequentially charged into a flask
  2. customequipped with a condenser and nitrogen inlet adapter

出典と根拠

ORDレコード
ord-b7422b77623e43858abc2bb907b837a8
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

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