Dichloromethane → HCID 86730673, 화합물

HRID 632655노트

반응식

HRID 632655 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](C=O)=[N:16][CH:17]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:36][C:37]([O:39][CH3:40])=[O:38])C=CC=CC=1.[CH2:53](Cl)Cl>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](/[CH:53]=[CH:36]/[C:37]([O:39][CH3:40])=[O:38])=[N:16][CH:17]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 867306725-((6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)picolinaldehyde

생성물 1

HCID 86730673HCID 86730673, 화합물수율 32%

실험 절차

To a solution of 5-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)picolinaldehyde (0.265 g, 0.68 mmol) in DCM (3.38 mL) at 0° C. was added methyl 2-(triphenylphosphoranylidene)acetate (0.543 g, 1.63 mmol) and the reaction was stirred at room temperature for 18 h. Upon completion the mixture was concentrated in vacuo to afford crude material which was purified by column chromatography (SiO2, 0-25% EtOAc/heptanes) to afford (E)-methyl 3-(5-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate (96 mg, 0.22 mmol, 32% yield). 1H NMR (400 MHz, CDCl3) δ ppm=3.70-3.75 (m, 6H), 3.79-3.83 (m, 3 H), 6.70 (d, J=15.66 Hz, 1 H), 6.77-6.88 (m, 3 H), 7.02 (dd, J=8.59, 3.03 Hz, 1 H), 7.17 (s, 1 H), 7.18-7.22 (m, 2 H), 7.48-7.59 (m, 3 H), 8.42 (d, J=2.53 Hz, 1 H). LC/MS (m/z, MH+): 448.3.

후처리

  1. concentrationUpon completion the mixture was concentrated in vacuo
  2. customto afford crude material which
  3. customwas purified by column chromatography (SiO2, 0-25% EtOAc/heptanes)

출처 및 근거

ORD 기록
ord-842b15bde121478da673379b2bbada07
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321746B2

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