Formic Acid → HCID 17816453, compound

HRID 2249698Notes

Reaction equation

HRID 2249698 reaction equation
Br[C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:8](=[O:16])[N:7]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]=2[CH:5]=[C:4](Br)[C:3]=1[C:23]([O:25][CH3:26])=[O:24].C(O)=O.C(N(CC)CC)C.Cl>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C>[CH2:17]([N:7]1[C:6]2[CH:5]=[CH:4][C:3]([C:23]([O:25][CH3:26])=[O:24])=[CH:2][C:10]=2[N:9]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:8]1=[O:16])[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

9

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 17816478HCID 17816478, compound

Product 1

HCID 17816453HCID 17816453, compoundYield 77.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In 7 ml of N,N-dimethylformamide are suspended 0.70 g of methyl 4,6-dibromo-1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate, 0.16 g of tetrakis(triphenylphosphine)palladium(0), 0.44 ml of formic acid and 2.4 ml of triethylamine. The suspension is stirred at 100° C. for 3 hours. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 4 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 0.37 g of methyl 1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate as a colorless oily product.

Workup

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-74901506a3a0406d9f6e947b3bde71a6
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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