4-Fluoro-2-nitrobenzaldehyde → 6-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole

HRID 334673Notes

Reaction equation

HRID 334673 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH3:13][Si:14]([CH3:21])([CH3:20])[C:15]#[C:16][CH2:17][CH2:18][NH2:19]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]2[C:4]([CH:3]=1)=[N:10][N:19]([CH2:18][CH2:17][C:16]#[C:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[CH:6]=2

Participants

3

Reactant 2

HCID 762264-Fluoro-2-nitrobenzaldehydeHCID 19703099(4-Aminobut-1-yn-1-yl)trimethylsilane

Product 1

HCID 665979056-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazoleYield 100%

Procedure

The title compound was prepared in accordance with the general method of Example 149(A), from 4-fluoro-2-nitro-benzaldehyde (180 mg, 1.06 mmol) and 4-trimethylsilanyl-but-3-ynylamine (200 mg, 1.40 mmol). The crude product was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 6-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole (310 mg, 1.06 mmol).

Workup

  1. customThe crude product was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-f6ea74b351a4457d838c70304d1e858d
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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