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3-Fluorobenzenesulfonyl Chloride → N-(3-cyano-1H-indazol-5-yl)-3-fluorobenzenesulfonamide

HRID 25359
Notes
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Reaction equation

HRID 25359 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]#[N:12].[F:13][C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>N1C=CC=CC=1>[C:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[CH:15]=3)(=[O:22])=[O:21])[CH:3]=2)[NH:7][N:6]=1)#[N:12]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 225673035-Amino-1H-indazole-3-carbonitrile

Product 1

HCID 10064331N-(3-cyano-1H-indazol-5-yl)-3-fluorobenzenesulfonamideYield 84.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(3-Cyano-1H-indazol-5-yl)-3-fluorobenzenesulfonamide can be obtained as described in Example 2 from 0.6 g of 5-amino-3-cyano-1H-indazole, 12 ml of pyridine and 0.73 g of 3-fluorobenzenesulfonyl chloride. 1 g of N-(3-cyano-1H-indazol-5-yl)-3-fluorobenzenesulfonamide is thus obtained in the form of a yellow solid melting at 227° C. (analysis C14H9FN4O2S % calculated C, 53.16; H, 2.87; F, 6.01; N, 17.71; O, 10.12; S, 10.14. % found C, 52.86; H, 2.63; F, 5.67; N, 16.04).

Sources & evidence

ORD record
ord-7eb43dc95b7a49faa926ff28d6263e41
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858638B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes