Methyl Thioglycolate → HCID 59253215, compound

HRID 1817890Notes

Reaction equation

HRID 1817890 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.C(N(CC)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 129.1%

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, 1.40 g, 4.36 mmol) in 1,4-dioxane (9 mL) were added N,N-diisopropylethylamine (1.52 mL, 8.72 mmol), methyl mercaptoacetate (0.39 ml, 4.36 mmol), tris(dibenzylideneacetone)dipalladium(0) (200 mg, 0.218 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (252 mg, 0.436 mmol). The mixture was heated to reflux for 21 h under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a dark brown syrup. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (1.95 g, quant.) as an orange syrup.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 21 h under nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto give a dark brown syrup
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1 as eluent)

Sources & evidence

ORD record
ord-fb104364e17e4b2eb314c1ff13b4d28f
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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