Carbon Dioxide → 7-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid Dimethylamide

HRID 969540Notes

Reaction equation

HRID 969540 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[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.[CH3:47][NH:48][CH3:49].[C:50](=[O:52])=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:47][N:48]([CH3:49])[C:50]([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][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]=2[CH:12]=1)=[O:52]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11776TriphenylphosphineHCID 462211624-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole

Product 1

HCID 462211637-Benzyloxy-2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazole-5-carboxylic Acid DimethylamideYield 65%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

5.8 g (13 mmol) 4-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole, 1.3 g (5.2 mmol) triphenylphosphine, 0.4 g (1.9 mmol) palladium(II) acetate and 80 ml (160 mmol) dimethylamine (2M in THF) 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 crystallization of the residue from diisopropyl ether afforded 3.7 g (65%) of the title compound as a white solid.

Workup

  1. customat 120° C.
  2. customfor 16 h
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crystallization of the residue from diisopropyl ether

Sources & evidence

ORD record
ord-4012a087390c4199acd52f25c093bb2d
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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