Carbon Dioxide → HCID 69134282, compound

HRID 969537Notes

Reaction equation

HRID 969537 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[N:14]([CH3:20])[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.[CH3:41][NH:42][CH3:43].[C:44](=[O:46])=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:41][N:42]([CH3:43])[C:44]([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]([CH2:18][CH3:19])[N:14]([CH3:20])[C:13]=2[CH:12]=1)=[O:46]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11776TriphenylphosphineHCID 69135170HCID 69135170, compound

Product 1

HCID 69134282HCID 69134282, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

10 g (29 mmol) 4-Benzyloxy-6-bromo-2-ethyl-1-methyl-1H-benzimidazole, 4.6 g (17.4 mmol) triphenylphosphine, 1.0 g (4.3 mmol) palladium(II) acetate in 145 ml (290 mmol) dimethylamine (2 M in THF) were transferred to an autoclave and carbonylated (6 bar CO2) at 120° C. for 24 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. Purification of the residue by column chromatography on silica gel (dichloromethane/methanol=93:7) and crystallization from diethyl ether afforded 11.3 g (91%) of the title compound as white crystals. m.p. 104°-108° C.

Workup

  1. customat 120° C.
  2. customfor 24 h
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the residue by column chromatography
  6. customon silica gel (dichloromethane/methanol=93:7) and crystallization from diethyl ether

Sources & evidence

ORD record
ord-6b75b37eed8c459b943f4213e12977b9
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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