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

HRID 1435588Notes

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

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 dissolved 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

temperaturethen cooled
filtrationfiltered through Celite®
customThe solvent was removed in vacuo
dissolutionthe residue dissolved in ethyl acetate (30 mL)
washwashed with saturated sodium bicarbonate (15 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record: ord-c2aab4ddb2814b2095dcf9c44970c476
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618964B2

Reaction notes

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