Tetrahydrofuran → HCID 67405268, compound

HRID 2069085Notes

Reaction equation

HRID 2069085 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C1COCC1.FC(F)(F)S(O[C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([Br:28])[CH:27]=1)[CH:24]=[N:23][CH:22]=[CH:21]2)(=O)=O.[C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)#[N:32]>[Cl-].[Na+].O.O.C(OCC)(=O)C.C(Cl)Cl>[Br:28][C:26]1[CH:27]=[C:18]([C:37]2[CH:38]=[C:33]([CH:34]=[CH:35][CH:36]=2)[C:31]#[N:32])[CH:19]=[C:20]2[C:25]=1[CH:24]=[N:23][CH:22]=[CH:21]2

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 86646483HCID 86646483, compound

Product 1

HCID 67405268HCID 67405268, compoundYield 62.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

An aqueous solution (50 mL) of sodium carbonate (3.5 g) was added to a THF (200 mL) solution of Intermediate 8 (3.9 g), 3-cyanophenylboronic acid (which may be referred to as sbo1; 1.6 g; WAKO), PdCl2dppf.CH2Cl2 (1.78 g; TCI) at room temperature and the resulting mixture was stirred as it was for 6 and half hours. Ethyl acetate (300 mL), saturated brine, and water were added to extract the reaction mixture, then the organic layer was dried, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (Yamazen; chloroform/methanol) to give the title compound (2.1 g).

Workup

  1. extractionto extract the reaction mixture
  2. customthe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography (Yamazen; chloroform/methanol)

Sources & evidence

ORD record
ord-b53f0c300b9a48ea8bd643ad4de88b8d
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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