2-Chloro-6-nitrobenzaldehyde → 4-chloro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole

HRID 334671Notes

Reaction equation

HRID 334671 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:3]=1[CH:4]=O.[CH3:13][Si:14]([CH3:21])([CH3:20])[C:15]#[C:16][CH2:17][CH2:18][NH2:19]>>[Cl:1][C:2]1[C:3]2[C:6]([CH:7]=[CH:8][CH:9]=1)=[N:10][N:19]([CH2:18][CH2:17][C:16]#[C:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[CH:4]=2

Participants

3

Reactant 2

HCID 807012-Chloro-6-nitrobenzaldehydeHCID 19703099(4-Aminobut-1-yn-1-yl)trimethylsilane

Product 1

HCID 665979934-chloro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazoleYield 43%

Procedure

The title compound was prepared in accordance with the general method of Example 149(A), from 2-chloro-6-nitro-benzaldehyde (210 mg, 1.13 mmol) and 4-trimethylsilanyl-but-3-ynylamine (210 mg, 1.50 mmol). The crude product was purified by flash chromatography (cyclohexane/AcOEt 92.5:7.5) to yield 4-chloro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole (134 mg, 0.48 mmol, 43%) as a yellow oil.

Workup

  1. customThe crude product was purified by flash chromatography (cyclohexane/AcOEt 92.5:7.5)

Sources & evidence

ORD record
ord-05537857762d4f57b163b5ee3e9e5bad
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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