Carbon Dioxide → HCID 69136056, compound

HRID 969529Notes

Reaction equation

HRID 969529 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:19][O:20][CH3:21])[C:13]=2[CH:12]=[CH:11][C:10]=1Br)[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>O1CCCC1.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]([CH3:18])[N:14]([CH2:19][O:20][CH3:21])[C:13]=2[CH:12]=1)=[O:47]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11776TriphenylphosphineHCID 69523158HCID 69523158, compound

Product 1

HCID 69136056HCID 69136056, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10.6 g (29.3 mmol) 4-Benzyloxy-bromo-1-methoxymethyl-2-methyl-1H-benzimidazole, 4.6 g (17.6 mmol) triphenylphosphine, 1.0 g (4.3 mmol) palladium(II) acetate, 148 ml (293 mmol) dimethylamine (2 M in THF) in 50 ml tetrahydrofuran were transferred to an autoclave and carbonylated (6 bar CO2) at 120° C. for 16 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. The purification of the residue by column chromatography on silica gel (dichloromethane/methanol=20:1) afforded 4.9 g (50%) of the title compound as a yellow oil.

Workup

  1. customat 120° C.
  2. customfor 16 h
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe purification of the residue by column chromatography on silica gel (dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-932ba3265e99404b8b607f910b186ca8
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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