[1-(2-Ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic Acid → Ethyl (4-oxo-4,5-dihydropyrrolo[2,3,4-if]isoquinolin-1(3H)-yl)acetate

HRID 551043노트

반응식

HRID 551043 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][C:16](O)=[O:17])[CH:11]=[CH:12][CH:13]=2)[C:8]([N+:19]([O-])=O)=[CH:7]1)[CH3:2]>CC(O)=O.O.[Fe]>[O:17]=[C:16]1[CH2:15][C:10]2[C:9]3=[C:14]([N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH:7]=[C:8]3[NH:19]1)[CH:13]=[CH:12][CH:11]=2

참가 물질

5

반응물 1

HCID 57426202[1-(2-Ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic Acid

생성물 1

HCID 59257910Ethyl (4-oxo-4,5-dihydropyrrolo[2,3,4-if]isoquinolin-1(3H)-yl)acetate

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a solution of [1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic acid from Step F (250 mg, 0.816 mmol) in AcOH (18 mL) and H2O (2 mL) was added iron powder (456 mg, 8.16 mmol) and the reaction mixture was heated at 80° C. for 18 h. The mixture was concentrated in vacuo to remove most of the solvent and the residue was partitioned between saturated aqueous NaHCO3 (5 mL) and EtOAc (25 mL). The organic layer was washed with brine, then dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound, which was of sufficient purity for use in the next step. MS: m/z=259 (M+1).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove most of the solvent
  3. customthe residue was partitioned between saturated aqueous NaHCO3 (5 mL) and EtOAc (25 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6be926cc14d942fb8c783edd77bbcf51
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947677B2

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