HCID 9934356, compound → 1H-Indole-5-acetic acid, 3-(ethoxycarbonyl)-2-methyl-, ethyl ester

HRID 2301331Notes

Reaction equation

HRID 2301331 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2=[C:11]3[C:20](=[C:21](Br)[CH:22]=[C:9]2[NH:8][C:7]=1[CH3:30])[CH2:19][CH:18]1N(CCC2C=C(OC)C=CC=21)C3)=[O:5])[CH3:2].C1C[O:34][CH2:33][CH2:32]1.C([OH:38])C>[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[C:9](=[CH:22][CH:21]=[C:20]([CH2:19][C:18]([O:34][CH2:33][CH3:32])=[O:38])[CH:11]=2)[NH:8][C:7]=1[CH3:30])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 9934356HCID 9934356, compoundHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 113237171H-Indole-5-acetic acid, 3-(ethoxycarbonyl)-2-methyl-, ethyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 5-bromo-9-methoxy-2-methyl-6,11,12,13-tetrahydro-3H,6aH-3,12a-diaza-benzo[a]cyclopent[h]anthracene-1-carboxylic acid ethyl ester (Example 1, Step 9) (0.2 g, 0.42 mmol) in THF/ethanol 1:1 (30 mL) is added palladium on carbon (20%). The suspension is hydrogenated for 8 hours. The catalyst is filtered and the solution is concentrated in vacuo. Ethanol (1 mL) is added and white crystals precipitated. The solid material is filtered and recrystallized from ethanol to afford the desired product (Compound 3) (0.09 g, 54%). MS: 391.1 (M+1)+.

Workup

  1. filtrationThe catalyst is filtered
  2. concentrationthe solution is concentrated in vacuo
  3. additionEthanol (1 mL) is added
  4. customwhite crystals precipitated
  5. filtrationThe solid material is filtered
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-323978b1eb8641f9af95d8ab28634b28
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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