Ethyl Acetate → 3-Fluoro-4-(6-(pyridine-4-yl)-1H-indazole-5-yloxy)aniline

HRID 1661982Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(2-fluoro-4-nitrophenoxy)-6-(pyridine-4-yl)-1H-indazole (1.95 g, 4.5 mmol) and SnCl2.2H2O (10.2 g, 45.3 mmol) in EtOAc/EtOH (200 mL/10 mL) is stirred at 80° C. for 2 hours. Then aqueous NaHCO3 and EtOAc are added. The organic phase is dried over anhydrous MgSO4 and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (2:1) to give the desired product (1.10 g, 61.0% yield). MS (m/z): 321.0 (M+H).

Workup

dry with materialThe organic phase is dried over anhydrous MgSO4
concentrationconcentrated
customThe residue is purified by silica gel column chromatography
washeluting with PE

Sources & evidence

ORD record: ord-48cc594eb1ef407f87b60aafbd8974bc
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030302B2

Reaction notes

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