4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-4-[4-chloro-2-(1H-pyrazol-4-yl)phenoxy]benzenesulfonamide

HRID 1692200Notes

Reaction equation

HRID 1692200 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[S:18][C:19]([Cl:22])=[CH:20][N:21]=3)(=[O:15])=[O:14])=[CH:9][C:8]=2[C:23]#[N:24])=[C:4](I)[CH:3]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][NH:39][CH:40]=2)O1>>[Cl:22][C:19]1[S:18][C:17]([NH:16][S:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][C:4]=3[C:36]3[CH:37]=[N:38][NH:39][CH:40]=3)=[C:8]([C:23]#[N:24])[CH:9]=2)(=[O:15])=[O:14])=[N:21][CH:20]=1

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 594364884-(4-chloro-2-iodophenoxy)-N-(5-chloro-1,3-thiazol-2-yl)-3-cyanobenzenesulfonamide

Product 1

HCID 46840817N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-4-[4-chloro-2-(1H-pyrazol-4-yl)phenoxy]benzenesulfonamide

Procedure

The title compound was prepared according to the same method as that used for Example 785 above using 4-(4-chloro-2-iodophenoxy)-N-(5-chloro-1,3-thiazol-2-yl)-3-cyanobenzenesulfonamide (Preparation 219) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole as starting materials. Purification by preparative HPLC afforded the title compound. Yield 7.8 mg 17%.

Workup

  1. customThe title compound was prepared
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-44a7b157c93740efb59ca533a5918f37
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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