Carbon Dioxide → HCID 69134410, compound

HRID 969523Notes

Reaction equation

HRID 969523 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH:18]([CH3:20])[CH3:19])[N:14]([CH3:21])[C:13]=2[CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:42][NH:43][CH3:44].[C:45](=[O:47])=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:42][N:43]([CH3:44])[C:45]([C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[N:16]=[C:15]([CH:18]([CH3:20])[CH3:19])[N:14]([CH3:21])[C:13]=2[CH:12]=1)=[O:47]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11776TriphenylphosphineHCID 69134395HCID 69134395, compound

Product 1

HCID 69134410HCID 69134410, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

5.6 g (15.5 mmol) 4-Benzyloxy-6-bromo-2-isopropyl-1-methyl-1H-benzimidazole, 2.4 g (3.3 mmol) triphenylphosphine, 521 mg (2.3 mmol) palladium(II) acetate and 78.5 ml (155 mmol) dimethylamine (2 M in THF) were transferred to an autoclave and carbonylated (6 bar CO2) at 120° C. for 3 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. Purification of the residue by column chromatography on silica gel (petroleum ether/ethyl acetate=1:5) afforded 3.8 g (70%) of the title compound as a yellow wax.

Workup

  1. customat 120° C.
  2. customfor 3 h
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the residue by column chromatography on silica gel (petroleum ether/ethyl acetate=1:5)

Sources & evidence

ORD record
ord-8b4c616ba48f474b96965ea64207124b
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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