Hydrochloric Acid → 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2234668Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:9]([C:13]2[N:14]([CH2:18][CH3:19])[N:15]=[CH:16][CH:17]=2)=[CH:10]OC)[C:5]([NH2:8])=[N:6][CH:7]=1.Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([C:13]3[N:14]([CH2:18][CH3:19])[N:15]=[CH:16][CH:17]=3)=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Bromo-3-[1-(2-ethyl-2H-pyrazol-3-yl)-2-methoxy-vinyl]-pyridin-2-ylamine (602 mg, 1.86 mmol), ethyl alcohol (30 ml), and concentration hydrochloric acid (30 ml) were combined and stirred at 100° C. for 18 hours. The reaction was quenched with sodium bicarbonate solution and the product was filtered off. The filtered product was dried under high vacuum to give 320 mg (59%) of 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine. MS: m/z 291.3+293.3 (M+H+).

Workup

customThe reaction was quenched with sodium bicarbonate solution
filtrationthe product was filtered off
customThe filtered product was dried under high vacuum

Sources & evidence

ORD record: ord-37ccabf124d047b9a6be206184050a1c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709645B2

Reaction notes

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