Triethylamine → (1-Methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(2-(trimethylsilyl)ethynyl)pyridin-2-yloxy)phenyl)methanone

HRID 410157Notes

Reaction equation

HRID 410157 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[N:21]([CH3:22])[C:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=4[N:18]=3)=[O:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:34][Si:35]([C:38]#[CH:39])([CH3:37])[CH3:36]>CN(C=O)C.C(Cl)Cl.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][N:21]1[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=[C:17]1[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]([C:39]#[C:38][Si:35]([CH3:37])([CH3:36])[CH3:34])=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1)=[O:16]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 59327020(4-(3-Bromopyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[D]imidazol-2-YL)methanone

Product 1

HCID 59327100(1-Methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(2-(trimethylsilyl)ethynyl)pyridin-2-yloxy)phenyl)methanone

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (4-(3-bromopyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone (0.18 g, 0.44 mmol), triethylamine (0.12 mL, 0.88 mmol), copper iodide (0.0084 g, 0.044 mmol), dichlorobis(triphenyl-phosphine)palladium (0.015 g, 0.022 mmol), trimethylsilylacetylene (0.093 mL, 0.66 mmol) in 1 mL DMF was heated to 110° C. overnight. The reaction mixture was diluted with DCM and then washed with water and brine. The organic layer was purified by silica gel chromatography (0-10% MeOH/DCM) to afford (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(2-(trimethylsilyl)ethynyl)pyridin-2-yloxy)phenyl)-methanone.

Workup

  1. washwashed with water and brine
  2. customThe organic layer was purified by silica gel chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-7d21e4da20cd49698502a81971fd772a
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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