3-[1-ethyl-5-(4-fluoro-2-nitrophenoxy)-1H-pyrazol-3-yl]benzonitrile → 3-[5-(2-amino-4-fluorophenoxy)-1-ethyl-1H-pyrazol-3-yl]benzonitrile

HRID 540758Notes

Reaction equation

[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[N+:16]([O-])=O)=[CH:6][C:5]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[N:4]1)[CH3:2].[H][H]>CO>[NH2:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])[CH:6]=1

Participants

Conditions

Temperature: 22 °C

Procedure

Pt/Vd (3%/0.6% wt/wt on carbon, 50 mg, 0.008 mmol, 0.005 equiv) was added to a stirring solution of 3-[1-ethyl-5-(4-fluoro-2-nitrophenoxy)-1H-pyrazol-3-yl]benzonitrile (0.54 g, 1.53 mmol, 1 equiv) in methanol (15.3 mL). A 3-way stop cock with a hydrogen balloon was installed and the reaction vessel was subjected to alternating vacuum and H2 gas (4×). The resulting mixture was stirred at 22° C. for 2 hours. The mixture was then subjected to alternating vacuum and nitrogen gas (4×) before the mixture was filtered through a nylon syringe filter and concentrated in vacuo to afford 3-[5-(2-amino-4-fluorophenoxy)-1-ethyl-1H-pyrazol-3-yl]benzonitrile. The crude reaction product was carried forward without further purification. Calcd (M+1)+: 323.1. Found: 323.0.

Workup

filtrationwas filtered through a nylon syringe
filtrationfilter
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-19af053e481742f9a328d929e7a5b17a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871796B2

Reaction notes

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