Triethylamine → HCID 18449401, compound

HRID 1675770Notes

Reaction equation

HRID 1675770 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17]2[S:18][CH:19]=[C:20](Br)[N:21]=2)[C:9]1=[O:23])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17]2[S:18][CH:19]=[C:20]([C:6]([O:5][CH3:1])=[O:24])[N:21]=2)[C:9]1=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86607786tert-Butyl [3-(4-bromo-1,3-thiazol-2-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

Product 1

HCID 18449401HCID 18449401, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl[3-(4-bromo-1,3-thiazol-2-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate from Step A (250 mg, 0.609 mmol) and triethylamine (0.850 mL, 6.09 mmol) in MeOH (5 mL) was added bis(triphenylphosphine)palladium (II) chloride (86.0 mg, 0.122 mmol). The reaction mixture was heated at reflux under an atmosphere of carbon monoxide (ca 1 atm) for 48 h, then partitioned between CHCl3 (20 mL) and saturated aqueous NaHCO3 (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 60:40, to give the title compound. MS: m/z=412 (M+23).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under an atmosphere of carbon monoxide (ca 1 atm) for 48 h
  3. custompartitioned between CHCl3 (20 mL) and saturated aqueous NaHCO3 (5 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-abcdae0e9f534e859185a8d9fa3d6030
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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