Potassium Carbonate → 1-methyl-3-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d]imidazol-2(3H)-one

HRID 334778Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15]1=[O:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]([CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:15]1=[O:23]

Participants

Conditions

Temperature: 50 °C

Procedure

2-(5-chloropent-1-ynyl)pyridine (59 mg, 0.33 mmol), 1-methyl-1H-benzo[d]imidazol-2(3H)-one (44 mg, 0.3 mmol) and K2CO3 (70 mg, 0.51 mmol) were poured into DMF (0.45 mL) and the resulting mixture was heated at 50° C. overnight. The mixture was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 40 mg of 1-methyl-3-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d]imidazol-2(3H)-one as a yellow oil (Yield: 43%).

Workup

customThe mixture was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)

Sources & evidence

ORD record: ord-83432cb15cee4409a8fe924eae9ae077
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883826B2

Reaction notes

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