Potassium Carbonate → 6-(3-chloro-4-nitrophenoxy)-1H-indazole

HRID 388994

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[N:18][NH:19]2)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[O:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[N:18][NH:19]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 2-chloro-4-fluoro-1-nitrobenzene (3 mmol) in DMF (5 mL) was added 6-hydroxyindazole (3 mmol) and K2CO3 (6 mmol). The contents were heated at 90° C. for 6 h. The reaction mixture was cooled to RT, and the contents were poured onto ice cold water with vigorous stirring. The solid formed was collected by filtration, washed with water, and dried in vacuo to provide the product, 6-(3-chloro-4-nitrophenoxy)-1H-indazole as a yellow solid, which was used for further transformation without any purification.

Workup

temperatureThe reaction mixture was cooled to RT
additionthe contents were poured onto ice cold water with vigorous stirring
customThe solid formed
filtrationwas collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-aa9c61eb9a0747b8bab51dd04a12563f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377983B2

Linked notes

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