Pyridine → HCID 20775760, compound

HRID 1015632Notes

Reaction equation

HRID 1015632 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 20775760HCID 20775760, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-Amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (1 g, 4.29 mmol) in dichloromethane (50 ml) was added phenyl boronic acid (1.05 g, 8.6 mmol), pyridine (680 mg, 8.6 mmol) and copper(II) acetate (1.18 g, 6.5 mmol). The reaction mixture was stirred for 16 h at room temperature. Then, the reaction mixture was filtered through celite, concentrated and the residue was purified by flash chromatography (9:1 Hexane/EtOAc) to obtain 435 mg (33%) of 5-Phenyl-3-phenylamino-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.38 ppm (dd, 2H, Haro); 7.35-7.26 ppm (m, 5H, Haro); 7.19 ppm (s, 1H, Haro); 7.15 ppm (dd, 2H, Haro); 7.02 ppm (ddt, 1H, Haro); 3.82 ppm (s, 3H).

Workup

  1. filtrationThen, the reaction mixture was filtered through celite,
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography (9:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-8cdc1d18629f45d9b1e5aa48cc37a446
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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