5-[6-(3-methoxy-prop-1-ynyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine → 5-[6-(3-methoxy-propyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 217601Notes

Reaction equation

HRID 217601 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][CH:7]=1>CO.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 595695945-[6-(3-methoxy-prop-1-ynyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 595695885-[6-(3-methoxy-propyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridineYield 77,210.703%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

5-[6-(3-Methoxy-prop-1-ynyl)-pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine (43, 0.534 g, 2.03 mmol) was dissolved in 8.1 mL of methanol. Palladium hydroxide (0.028 g, 0.20 mmol) was added, and the resulting mixture was stirred under an atmosphere of hydrogen for a few hours, then filtered through a bed of celite. The filtrate was concentrated under vacuum. The crude material was purified by silica gel flash chromatography eluting with ethyl acetate and hexane. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (44, 419 g). MS (ESI) [M+H+]+=268.3.

Workup

  1. filtrationfiltered through a bed of celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customThe crude material was purified by silica gel flash chromatography
  4. washeluting with ethyl acetate and hexane
  5. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-e07c8e5fa5cc4953b60a46ae716519ea
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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