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

HRID 1189267Notes

Reaction equation

HRID 1189267 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][Si:20]([CH3:25])([CH3:24])[C:21]#[C:22][CH3:23]>>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][CH2:23][C:22]#[C:21][Si:20]([CH3:25])([CH3:24])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 5634361-Benzyl-2-chloromethyl-1H-benzoimidazole

Product 1

HCID 665980051-benzyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazoleYield 102.4%

Procedure

The title compound was prepared in accordance with the general method of Example 191(D), from of 1-benzyl-2-(chloromethyl)-1H-benzo[d]imidazole (500 mg, 1.9 mmol) and trimethyl(prop-1-ynyl)silane (262 mg, 2.34 mmol). 1-benzyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazole (647 mg, Yield: 100%) was obtained as a brown oil which was used in the next step without purification.

Sources & evidence

ORD record
ord-c82c574a8a8e47a6bab3b3414f206a28
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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