Water → 5-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HRID 347385ノート

反応式

HRID 347385 の反応式
[CH:1]([C:3]1[C:4]([O:23][CH3:24])=[CH:5][C:6]([O:21][CH3:22])=[C:7]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:18](=[O:20])[CH3:19])[CH:8]=1)=[O:2].CN(C=O)C.O>[Pd](Cl)Cl.CCOC(C)=O>[C:18]([N:17]1[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[C:9]1[C:7]1[C:6]([O:21][CH3:22])=[CH:5][C:4]([O:23][CH3:24])=[C:3]([CH:8]=1)[CH:1]=[O:2])(=[O:20])[CH3:19]

参加物

6

反応物 3

HCID 962WaterHCID 6228DimethylformamideHCID 11438686N-[2-(5-formyl-2,4-dimethoxyphenylethynyl)phenyl]acetamide

生成物 1

HCID 210825305-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde収率 40.6%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

N-[2-(5-Formyl-2,4-dimethoxy-phenyl ethynyl)phenyl]acetamide (Ex-57E, 535 mg, 1.6 mmol) was added to 150 mL of DMF (nitrogen purged) at room temperature and the resulting solution was heated to 80° C. Palladium(II) chloride (22 mg) was added in one portion. After 6 h the reaction mixture was poured into water (50 mL) and EtOAc (50 mL), and the layers were cut. The organic layer was filtered through Celite, washed with brine, and concentrated to an orange solid. The crude was purified by silica gel chromatography (25% ethyl acetate/hexane) to yield 210 mg (39%) of 5-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde as a white solid. 1H-NMR (300 MHz, DMSO-d6) 10.22 (s, 1H), 8.13 (d, 1H, J=8.1 Hz), 7.71 (s, 1H), 7.55 (d, 1H, J=6.3 Hz), 7.25 (m, 2H, J=6.9 Hz), 6.84 (s, 1H), 6.64 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 2.13 (s, 3H).

後処理

  1. filtrationThe organic layer was filtered through Celite
  2. washwashed with brine
  3. concentrationconcentrated to an orange solid
  4. customThe crude was purified by silica gel chromatography (25% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-1694fb05fc7d4adeb6d8af77eb19a6be
出典データセット
uspto-grants-2007_02
特許番号
US07173129B2

反応ノート

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