Trimethylsilylacetylene → HCID 178504179, compound

HRID 1615102Notes

Reaction equation

HRID 1615102 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24](I)=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([Si:29]([CH3:32])([CH3:31])[CH3:30])#[CH:28]>CN(C=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:27]#[CH:28])=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:28]#[C:27][Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178525131HCID 178525131, compound

Product 2

HCID 178435594HCID 178435594, compoundHCID 178504179HCID 178504179, compoundYield 138.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (S)-2-(5-iodo-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (524 mg, 1.135 mmol), CuI (22 mg, 0.114 mmol) and bis(triphenylphosphine)palladium(II)dichloride (40 mg, 0.056 mmol) in DMF (4 mL) is added TEA (0.47 mL, 3.4 mmol) followed by ethynyl-trimethylsilane (0.17 mL, 1.25 mmol). The reaction mixture is stirred at room temperature overnight and concentrated in vacuum to dryness. The residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 5% to 100%) to give a yellow residue which is triturated twice with DCM to afford the title compound (S)-2-(5-trimethylsilanylethynyl-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (340 mg, 70%).

Workup

  1. concentrationconcentrated in vacuum to dryness
  2. customThe residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 5% to 100%)
  3. customto give a yellow residue which
  4. customis triturated twice with DCM

Sources & evidence

ORD record
ord-570c15ed8626455f994d124cdd0e7883
Source dataset
uspto-grants-2014_07
Patent number
US08765731B2

Reaction notes

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