(4-Aminobut-1-yn-1-yl)trimethylsilane → 7-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole

HRID 1189206Notes

Reaction equation

HRID 1189206 reaction equation
[F:1][C:2]1[C:3]([N+:10]([O-])=O)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:13][Si:14]([CH3:21])([CH3:20])[C:15]#[C:16][CH2:17][CH2:18][NH2:19]>>[F:1][C:2]1[C:3]2[C:4](=[CH:5][N:19]([CH2:18][CH2:17][C:16]#[C:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[N:10]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 19703099(4-Aminobut-1-yn-1-yl)trimethylsilaneHCID 224653213-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 665983617-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazoleYield 37.5%

Procedure

The title compound was prepared in accordance with the general method of Example 149(A), from 3-fluoro-2-nitro-benzaldehyde (0.2 g, 1.2 mmol) and 4-trimethylsilanyl-but-3-ynylamine (0.22 g, 1.5 mmol). The crude product was purified by flash chromatography (cyclohexane/AcOEt 92.5:7.5) to yield 7-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole (117 mg, 0.45 mmol) 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-ef8dea9859094b0191efacf9a075316c
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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