Carbon Dioxide → HCID 69135057, compound

HRID 969524Notes

Reaction equation

HRID 969524 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[N:14]([CH3:22])[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.[CH3:43][NH:44][CH3:45].[C:46](=[O:48])=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:43][N:44]([CH3:45])[C:46]([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]([C:18]([F:21])([F:20])[F:19])[N:14]([CH3:22])[C:13]=2[CH:12]=1)=[O:48]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11776TriphenylphosphineHCID 69134405HCID 69134405, compound

Product 1

HCID 69135057HCID 69135057, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

15.8 g (41.0 mmol) 4-Benzyloxy-6-bromo-1-methyl-2-trifluoromethyl-1H-benzimidazole, 6.4 g (24.6 mmol) triphenylphosphine, 1.4 g (6.2 mmol) palladium(II) acetate and 205 ml (410 mmol) dimethylamine (2 M 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. Purification of the residue by column chromatography on silica gel (dichloromethane/methanol=50:1) afforded 9.3 g (62%) of the title compound as a white solid. m.p. 144°-146° C.

Workup

  1. customat 120° C.
  2. customfor 16 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 (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-fa45b0457c8340acb720fc1c6d43fbc2
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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