[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 641407Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-0af068e1193e4e4b9c2652c16b2deb95
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696192B2

Reaction notes

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