Cesium carbonate → 5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-benzoxazole

HRID 1916765Notes

Reaction equation

HRID 1916765 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:7][C:6]=2[CH:16]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[CH:31])=[N:28][CH:29]=2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.[Cu]I>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[C:31][C:2]3[CH:3]=[CH:4][C:5]4[O:9][C:8]([CH2:10][N:11]5[CH2:15][CH2:14][CH2:13][CH2:12]5)=[N:7][C:6]=4[CH:16]=3)=[N:28][CH:29]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 690723805-Iodo-2-pyrrolidin-1-ylmethyl-benzoxazole

Product 1

HCID 598359025-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-benzoxazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of 260 mg (0.792 mmol) 5-iodo-2-pyrrolidin-1-ylmethyl-benzoxazole, 171 mg (0.8 mmol) 5-(4-chloro-phenyl)-2-ethynyl-pyridine, 23 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium, 3.8 mg (0.02 mmol) CuI and 350 mg (1.075 mmol) Cs2CO3 in 10 mL THF is stirred for 14 h in an argon atmosphere at RT. Then the reaction mixture is evaporated down and the residue is purified by column chromatography on silica gel (DCM/MeOH 80:1).

Workup

  1. customThen the reaction mixture is evaporated down
  2. customthe residue is purified by column chromatography on silica gel (DCM/MeOH 80:1)

Sources & evidence

ORD record
ord-c6008b3639ab4a96975fb4b5ba5dfccf
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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