Phenylacetylene → HCID 58387189, compound

HRID 1045111Notes

Reaction equation

HRID 1045111 reaction equation
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1.[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)#[CH:25].CCOC(C)=O.CO>CN(C=O)C.[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>[Cl:1][C:2]1[C:3]([C:25]#[C:24][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1

Participants

7

Reactant 3

HCID 10821PhenylacetyleneHCID 21584119Ethylacetate methanolHCID 59267806HCID 59267806, compound2×

Product 1

HCID 58387189HCID 58387189, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A 4 mL vial equipped with a stirring bar was charged with copper iodide (2.0 mg, 10 mol %), and Pd(PPh3)2Cl2 (3.5 mg, 5 mol %). A solution of 6-chloro-5-iodo-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (Intermediate 5, 49.0 mg, 0.100 mmol) in DMF (0.5 mL) was added to the vial, followed by a solution of ethynyl-benzene (20.0 mg, 0.200 mmol) in DMF (0.5 mL) and TEA (98 uL, 0.70 mmol). The resulting suspension was stirred at rt for 10 min, during which time it gradually turned brown. The solvent was then removed in vacuo to give brown oily solid, which was suspended in 1:1 EtOAc/MeOH (3 mL) and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The resulting solution was evaporated to dryness in vacuo to give light yellow oil. LR-MS (API-ES): calculated C22H25ClN2O3SSi 460.1, m/e (M+H)+ not observed, 433.0, 403 (Rt 3.83 min).

Workup

  1. customA 4 mL vial equipped with a stirring bar
  2. customThe solvent was then removed in vacuo
  3. customto give brown oily solid, which
  4. customThe resulting solution was evaporated to dryness in vacuo
  5. customto give light yellow oil

Sources & evidence

ORD record
ord-62dbfb4403b744349bdafda000f8a832
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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