HCID 89925481, compound → HCID 89925398, compound

HRID 922478Notes

Reaction equation

HRID 922478 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=[CH:10][C:9]=2[C:8]([CH:20]=[CH2:21])=[CH:7]1>C(O)C.[Pd]>[CH2:20]([C:8]1[C:9]2[CH:10]=[N:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][C:14]=2[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=1)[CH3:21]

Participants

4

Reactant 1

HCID 89925481HCID 89925481, compound

Product 1

HCID 89925398HCID 89925398, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-(3-methoxypropyl)-3-vinyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (460 mg) in ethanol (9 mL) was added 10% palladium on carbon (92 mg), and the mixture was stirred under hydrogen for 1 hour. An insoluble was filtered off, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1) to give ethyl 3-ethyl-1-(3-methoxypropyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(106-2)] (294 mg) as a yellow oil.

Workup

  1. filtrationAn insoluble was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1)

Sources & evidence

ORD record
ord-3af9e4f228604f529444322daa069c8a
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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