Selenious Acid → 5-Chloro-4-ethoxycarbonylmethyl-2-formyl-indole-1-carboxylic acid methyl ester

HRID 1161887

반응식

HRID 1161887 반응식
[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:21])=[O:4].[Se](O)(O)=[O:23]>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:21]=[O:23])=[O:4]

참가 물질

5

반응물 2

HCID 1091Selenious AcidHCID 668201565-Chloro-4-ethoxycarbonylmethyl-2-methyl-indole-1-carboxylic acid methyl ester

생성물 1

HCID 866038735-Chloro-4-ethoxycarbonylmethyl-2-formyl-indole-1-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

5-Chloro-4-ethoxycarbonylmethyl-2-methyl-indole-1-carboxylic acid methyl ester (398 mg, 1.28 mmol) is dissolved under an atmosphere of argon in dioxane (18 ml). Selenious acid (331 mg, 2.56 mmol) is added, and the reaction mixture is heated to 100° C. for 18 hours. TLC analysis indicates complete conversion of the starting material. The reaction mixture is diluted with EtOAc and poured on water. The organic layer is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated. The solid residue is purified by FCC (hexane/EtOAc 2:1) to afford the title compound. 1H NMR (DMSO, 400 MHz) δ 1.20 (t, J=6.6 Hz, 3H), 4.09 (s, 3H), 4.12 (q, J=6.6 Hz, 2H), 4.19 (s, 2H), 7.64 (d, J=10.8, 1H), 8.09 (d, J=10.8, 1H), 10.32 (s, 1H); ES-MS: 346.1.1 [M+Na]+.

후처리

  1. additionpoured on water
  2. washThe organic layer is washed with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe solid residue is purified by FCC (hexane/EtOAc 2:1)

출처 및 근거

ORD 기록
ord-8fa564b97d724679a1570eb4d623a91f
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820672B2

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