Dimethylformamide → HCID 17927102, compound

HRID 1592395Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1.[Li]C(C)(C)C.CN([CH:26]=[O:27])C.C([O-])(O)=O.[Na+]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH:26]=[O:27]

Participants

Conditions

Temperature: -40 °C

Procedure

Under an atmosphere of Ar, 1-(2-pyridin-2-yl-ethyl)-1H-benzimidazole (0.46 g, 2.1 mmol) (Ichikawa, M. et al. Chem. Pharm. Bull. 1981, 29, 3042-7) was dissolved in anhydrous THF (10 mL), cooled to −40° C., and treated with tert-BuLi (1.5 mL, 1.7M, 2.5 mmol) for 30 minutes. DMF (0.80 mL, 10.3 mmol) was then added and the solution slowly warmed to room temperature. After 1 hour, water (10 mL) and saturated aqueous NaHCO3 solution (10 mL) were added and the medium was extracted with EtOAc (3×25 mL). The combined organic phases were then dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was then purified by column chromatography with silica gel (50:1:0.1 MeOH:NH4OH:CH2Cl2) to afford 1-(2-pyridin-2-yl-ethyl)-1H-benzimidazole-2-carbaldehyde as a brown liquid that was used immediately in the next reaction (147 mg, 28%).

Workup

temperaturethe solution slowly warmed to room temperature
extractionthe medium was extracted with EtOAc (3×25 mL)
dry with materialThe combined organic phases were then dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was then purified by column chromatography with silica gel (50:1:0.1 MeOH:NH4OH:CH2Cl2)

Sources & evidence

ORD record: ord-4e306c2edbb04c68bd78b68c2ea25587
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291631B2

Reaction notes

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