Hydrochloric Acid → 2-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamine

HRID 502798Notes

Reaction equation

HRID 502798 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[NH:23][C:15]3=[N:16][CH:17]=[C:18]([N+:20]([O-])=O)[CH:19]=[C:14]3[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.Cl.O>C(O)C.[Fe]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[NH:23][C:15]3=[N:16][CH:17]=[C:18]([NH2:20])[CH:19]=[C:14]3[CH:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 684671552-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 684656192-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamineYield 60%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine (7.1 mmol, 2.2 g) and iron powder (6.7 g) in ethanol (50 mL) was added HCl (conc) (0.7 mL) and water (5 mL). The mixture was heated at 70° C. for 3 hours then cooled and filtered through Celite®. The solvent was removed in vacuo and the residue resolvated in ethyl acetate (30 mL), washed with saturated sodium bicarbonate (15 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2, ethyl acetate) to afford 2-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamine (1.2 g, 60%).

Workup

  1. temperaturethen cooled
  2. filtrationfiltered through Celite®
  3. customThe solvent was removed in vacuo
  4. washwashed with saturated sodium bicarbonate (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-18c3be9c06e64bdb99c4252a3d8d856d
Source dataset
uspto-grants-2010_08
Patent number
US07776878B2

Reaction notes

Loading…