Hexane → 7-chloro-1-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazole

HRID 334724Notes

Reaction equation

HRID 334724 reaction equation
[CH3:1][Si:2]([CH3:7])([CH3:6])[C:3]#[C:4][CH3:5].[Li]CCCC.CCCCCC.[Cl:19][C:20]1[C:25]2[N:26]([CH3:31])[C:27]([CH2:29]Cl)=[N:28][C:24]=2[CH:23]=[CH:22][CH:21]=1>C1COCC1>[Cl:19][C:20]1[C:25]2[N:26]([CH3:31])[C:27]([CH2:29][CH2:5][C:4]#[C:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[N:28][C:24]=2[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 803631-(Trimethylsilyl)prop-1-yneHCID 436599277-chloro-2-(chloromethyl)-1-methyl-1H-benzo[d]imidazoleHCID 178418339Butyllithium

Product 1

HCID 665983917-chloro-1-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the trimethyl(prop-1-ynyl)silane (0.21 mL, 1.4 mmol) in THF (4 mL), was added at −78° C. nBuLi 2.5M in hexane (0.56 mL, 1.3 mmol). After 90 min at −78° C., a solution of 7-chloro-2-(chloromethyl)-1-methyl-1H-benzo[d]imidazole (250 mg, 1.2 mmol) in THF (2 mL) was added. Mixture went from purple to orange and then dark brown. The reaction was quenched after 1 h at −78° C. with water and the solvent was evaporated to dryness to afford 338 mg of 7-chloro-1-methyl-2-(4-(trimethylsilyl)but-3-ynyl)-1H-benzo[d]imidazole (Yield: 100%) as a brown oily solid. It was carried through to the next step without purification.

Workup

  1. customThe reaction was quenched after 1 h at −78° C. with water
  2. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-aaef67279c114c3997882e47df318479
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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