Methyl Thioglycolate → HCID 59253215, compound

HRID 643710Notes

Reaction equation

HRID 643710 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:8][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[SH:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH:15]1([CH2:14][N:6]2[C:5]3[CH:18]=[CH:19][C:2]([S:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:3][C:4]=3[N:8]=[C:7]2[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 16907Methyl ThioglycolateHCID 81531DiisopropylethylamineHCID 58513608HCID 58513608, compound

Product 1

HCID 59253215HCID 59253215, compoundYield 109.7%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (Step D, 4.0 g, 12.5 mmol) in 1,4-dioxane (25 mL) were added N,N′-diisopropylethylamine (4.4 mL, 25 mmol), methyl mercaptoacetate (1.1 ml, 12.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (284 mg, 0.31 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (362 mg, 0.63 mmol). The mixture was stirred at reflux temperature for 24 h under nitrogen atmosphere. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 as eluent) to afford the title compound (4.75 g, quant.) as a pale yellow oil.

Workup

  1. temperatureat reflux temperature for 24 h under nitrogen atmosphere
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 as eluent)

Sources & evidence

ORD record
ord-64070399ebf6430caa25df03d365faed
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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