Sodium Carbonate → 1132638-92-6

HRID 1880405Notes

Reaction equation

HRID 1880405 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]2[N:9]=[C:8]([CH3:10])[NH:7][C:6]=2[CH:11]=1.[C:13]([O-])([O-:15])=[O:14].[Na+].[Na+]>O1CCOCC1.O.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH3:10][C:8]1[NH:7][C:6]2[CH:11]=[C:2]([C:13]([OH:15])=[O:14])[CH:3]=[C:4]([CH3:12])[C:5]=2[N:9]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 669204475-bromo-2,7-dimethyl-1H-1,3-benzodiazole

Product 1

HCID 669203951132638-92-6Yield 57%

Reagents, catalysts & solvents 4

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
165 °C

Procedure

To a solution of 6-bromo-2,4-dimethyl-1H-benzimidazole (200 mg, 0.90 mmol) in degassed dioxane (2 mL) was added ((trans-bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II))) (30 mg, 0.05 mmol), molybdenum hexacarbonyl (120 mg, 0.45 mmol) and a solution of Na2CO3 (283 mg, 2.67 mmol) in degassed water (2.4 ml). The mixture was stirred for 20 seconds and then heated at 165° C. for 15 minutes in a microwave reactor with absorption set at very high for 20 minutes. The reaction vessel was vented and filtered through diatomaceous earth. The solution was extracted with EtOAc and the aqueous phase was back extracted with additional EtOAc (2×). The combined organic extracts were set aside. Water (5 mL) was added to the aqueous extract which was then acidified with 0.5 M HCl to pH 3. The resulting solids were air dried to provide the title compound (97 mg, 57%).

Workup

  1. customvery high for 20 minutes
  2. filtrationfiltered through diatomaceous earth
  3. extractionThe solution was extracted with EtOAc
  4. extractionthe aqueous phase was back extracted with additional EtOAc (2×)
  5. additionWater (5 mL) was added to the
  6. extractionaqueous extract which
  7. customdried

Sources & evidence

ORD record
ord-b60917afff51491abcdd77ffdd8f5f12
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

Loading…