Pyridine → HCID 86583553, compound

HRID 1841749Notes

Reaction equation

HRID 1841749 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH:19]([C:25]2[CH:30]=[C:29]([OH:31])[CH:28]=[C:27]([CH2:32][CH3:33])[CH:26]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1)#[N:11].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH:19]([C:25]2[CH:30]=[C:29]([O:31][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:28]=[C:27]([CH2:32][CH3:33])[CH:26]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1)#[N:11]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 86583554HCID 86583554, compound

Product 1

HCID 86583553HCID 86583553, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper(II) acetate (223 mg, 1.20 mmol), phenylboronic acid (164 mg, 1.32 mmol) and molecular sieve 4 Å were added to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-5-hydroxy-phenyl)-acetate (390 mg, 1.20 mmol) obtained in Example 200.1 in CH2Cl2 (12 ml). Pyridine (476 mg, 6.01 mmol) was added dropwise and the mixture was stirred for 60 h. under an atmosphere of air. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, CH2Cl2). There were obtained 391 mg (81%) of ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-5-phenoxy-phenyl)-acetate as beige crystals; MS: 401 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-039a08ed9072493a92d691c5d453f606
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

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