HCID 58172079, compound → HCID 58172076, compound

HRID 560179Notes

Reaction equation

HRID 560179 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([N+:26]([O-])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([NH2:26])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 58172079HCID 58172079, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58172076HCID 58172076, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Nitro-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (prepared by the procedure described in Example 2 for the 5-bromo analog) (426 mg) was dissolved in 20 mL of methanol. Palladium on carbon (85 mg) was added and the flask was seal with a rubber septum. A vacuum was pulled through a needle and the void was refilled from a balloon of hydrogen gas. The resulting mixture was stirred under 1 atm of hydrogen gas for 17 h. In the morning, LCMS analysis revealed consumption of the starting material and formation of the product. The reaction mixture was filtered through diatomaceous earth and concentrated under vacuum to yield 5-amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester as an orange foam (432 mg, solvent trapped within). This material was used without further manipulation.

Workup

  1. customthe flask was seal with a rubber septum
  2. customconsumption of the starting material and formation of the product
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ac84307fce894c198597c3e863f72b70
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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