Hydrochloric Acid → 4-[1-ethyl-4-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline

HRID 1821233Notes

Reaction equation

[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]3[NH:15][CH:16]=[CH:17][C:9]=23)[C:5]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[N:4]1)[CH3:2].[Sn].Cl>C(O)C>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]3[NH:15][CH:16]=[CH:17][C:9]=23)[C:5]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (0.655 mmol) in ethanol (3.5 mL) was added tin(0) powder (3.28 mmol) and 6N aqueous hydrochloric acid (3.5 mL) and the mixture was heated to 70° C. for 1 h. The reaction mixture was allowed to cool to room temperature, filtered through a pad of celite. The filtrate was diluted with ethyl acetate (10 mL) and washed with 1N sodium hydroxide (5 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL) and the combined extracts were dried over sodium sulfate, filtered through a pad of celite and concentrated under reduced pressure to give the title compound as a yellow solid which was used without further purification. ESMS [M+H]+: 322

Workup

temperatureto cool to room temperature
filtrationfiltered through a pad of celite
additionThe filtrate was diluted with ethyl acetate (10 mL)
washwashed with 1N sodium hydroxide (5 mL)
extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
dry with materialthe combined extracts were dried over sodium sulfate
filtrationfiltered through a pad of celite
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8713a7833a034b28a4f20b473022a25a
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605266B2

Reaction notes

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