Cesium carbonate → HCID 18950398, compound

HRID 1492486Notes

Reaction equation

HRID 1492486 reaction equation
Br[CH2:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:20]([C:24]1[NH:25][C:26]([CH:30]=[O:31])=[C:27]([Cl:29])[N:28]=1)[CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:20]([C:24]1[N:25]([CH2:2][C:3]2[C:11]3[N:10]=[CH:9][N:8]([C:12]4[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=4[C:14]#[N:15])[C:7]=3[CH:6]=[CH:5][CH:4]=2)[C:26]([CH:30]=[O:31])=[C:27]([Cl:29])[N:28]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18950405HCID 18950405, compoundHCID 178418251HCID 178418251, compound

Product 1

HCID 18950398HCID 18950398, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-(Bromomethyl)-1H-benzimidazol-1-yl]-benzonitrile (0.65 g, 2.08 mmol, prepared as described in part C of Example 8) and 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.409 g, 2.19 mmol, prepared as described in part C of Example 5) were placed in 20.8 mL anhydrous dimethylformamide. Freshly ground cesium carbonate (1.02 g, 3.12 mmol) was then added and the reaction was stirred at room temperature for 16 hours. The reaction was then partitioned between ethyl acetate and water and the organic phase was washed with brine, dried and concentrated. The crude oil was purified by flash chromatography (SiO2, 80:20 hexane:acetone) to yield the title A compound (0.68 g) as a white solid.

Workup

  1. customThe reaction was then partitioned between ethyl acetate and water
  2. washthe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude oil was purified by flash chromatography (SiO2, 80:20 hexane:acetone)

Sources & evidence

ORD record
ord-4b7db66e62184f47a763b94320cd0086
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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