Pyridine → HCID 20775760, compound

HRID 2193916Notes

Reaction equation

HRID 2193916 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-e580e53fd5764a0ca643097f12092ed5
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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