Triethylamine → Ethyl 2-anilino-5-phenylthiophene-3-carboxylate

HRID 1967156Notes

Reaction equation

HRID 1967156 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[NH:1]([C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 638860ethyl 2-amino-5-phenylthiophene-3-carboxylate

Product 1

HCID 58256479Ethyl 2-anilino-5-phenylthiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A vial was charged with copper acetate (77 mg, 0.425 mmol), ethyl 2-amino-5-phenylthiophene-3-carboxylate (100 mg, 0.404 mmol), phenylboronic acid (99 mg, 0.809 mmol), dichloromethane (2 ml), and triethylamine (0.113 ml, 0.809 mmol). The blue-green reaction mixture was magnetically stirred for 19 hours and then concentrated to a volume of 0.5 mL. The crude reaction mixture was purified by silica gel chromatography (7-60% dichloromethane/hexanes) to afford ethyl 2-anilino-5-phenylthiophene-3-carboxylate.

Workup

  1. concentrationconcentrated to a volume of 0.5 mL
  2. customThe crude reaction mixture
  3. customwas purified by silica gel chromatography (7-60% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-617977799adc4f2cb87484740037c563
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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