1-(Trimethylsilyl)prop-1-yne → 5-fluoro-1-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazole

HRID 1189271Notes

Reaction equation

HRID 1189271 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:5]=2[N:4]=1.[CH3:14][Si:15]([CH3:20])([CH3:19])[C:16]#[C:17][CH3:18]>>[F:13][C:11]1[CH:10]=[CH:9][C:6]2[N:7]([CH3:8])[C:3]([CH2:2][CH2:18][C:17]#[C:16][Si:15]([CH3:20])([CH3:19])[CH3:14])=[N:4][C:5]=2[CH:12]=1

Participants

3

Reactant 2

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 436599262-(chloromethyl)-5-fluoro-1-methyl-1H-benzo[d]imidazole

Product 1

HCID 665983385-fluoro-1-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazoleYield 100%

Procedure

The title compound was prepared in accordance with the general method of Example 191(D), from of 2-(chloromethyl)-5-fluoro-1-methyl-1H-benzo[d]imidazole (270 mg, 1.36 mmol) and trimethyl(prop-1-ynyl)silane (183 mg, 1.63 mmol). The crude residue was used in the next step without any purification. 5-fluoro-1-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazole (373 mg, Yield: 100%) as a brown oil.

Workup

  1. customThe crude residue was used in the next step without any purification

Sources & evidence

ORD record
ord-705c1c2c9b0048ef97211761c519e88b
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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