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

HRID 347385노트

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HRID 347385 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1694fb05fc7d4adeb6d8af77eb19a6be
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173129B2

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