Methyl Thioglycolate → HCID 86604771, compound

HRID 1817897Notes

Reaction equation

HRID 1817897 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]2[N:6]([CH2:14][CH:15]3[CH2:20][CH2:19][O:18][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:32][CH2:33][C:34]([O:36][CH3:37])=[O:35].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>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]>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:7]1[N:6]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[CH:21]=[CH:22][C:2]([S:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:3][C:4]=2[N:8]=1

Participants

7

Reactant 4

HCID 16907Methyl ThioglycolateHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68871292HCID 68871292, compound

Product 1

HCID 86604771HCID 86604771, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-2-(2,2-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole (Step C, 300 mg, 0.82 mmol), N,N-diisopropylethylamine (286 μL, 1.64 mmol), methyl mercaptoacetate (73 μL, 0.82 mmol), tris(dibenzylideneacetone)dipalladium(0) (37.5 mg, 0.041 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (47.4 mg, 0.082 mmol) in 1,4-dioxane was microwaved at 120° C. for 30 min. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2 then 1:1 as eluent) to afford the title compound (318 mg, 99%) as a yellow viscous oil.

Workup

  1. customwas microwaved at 120° C. for 30 min
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-e01aa0bb6237468a9931a8583ca02be0
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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