Dimethylformamide → HCID 57785871, compound

HRID 1398972Notes

Reaction equation

HRID 1398972 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][C:14]4[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]=4[N:11]3[CH2:10][CH2:9]2)=[C:4]([Cl:26])[CH:3]=1.C([Li])CCC.CN(C)[CH:34]=[O:35]>O1CCCC1>[Cl:26][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[C:12]2=[N:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]=3[N:11]2[CH2:10][CH2:9]1)[CH:34]=[O:35]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 57785826HCID 57785826, compoundHCID 178418339Butyllithium

Product 1

HCID 57785871HCID 57785871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-bromo-2-chlorophenyl)-8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (204.6 mg, 0.451 mmol) in tetrahydrofuran (3.0 mL) was added n-butyllithium (1.60 M solution in n-hexane, 0.34 mL, 0.542 mmol) at −78° C. The reaction mixture was stirred at same temperature for 1 hr, to the mixture was added N,N-dimethylformamide (0.17 mL, 2.255 mmol). The reaction mixture was allowed to warm to 0° C. and stirred for 1 hr. The reaction mixture was quenched with aqueous saturated ammonium chloride at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with water (×2) and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow amorphous (89.5 mg, 0.156 mmol, 49%).

Workup

  1. stirringstirred for 1 hr
  2. customThe reaction mixture was quenched with aqueous saturated ammonium chloride at 0° C.
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with water (×2) and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-9dc972675b7e4c6a80ec53db8141273a
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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