Dibutyltin dichloride → 3-(1-Cyclohexyl-2-ethoxycarbonyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 579193Notes

Reaction equation

HRID 579193 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=O)[CH3:2].[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][C:23]=1[NH2:24])=[O:18].[Sn](Cl)(Cl)(CCCC)CCCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][C:23]=1[NH:24][CH:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])=[O:18]

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 266327Ethyl 3-cyclohexyl-3-oxopropanoateHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 666841133-(1-Cyclohexyl-2-ethoxycarbonyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl esterYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Cyclohexyl-3-oxo-propionic acid ethyl ester (1.0 g, 5.0 mmol, 1.0 equiv) in THF (5.0 mL) was added 3-Amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (1.17 g, 5.0 mmol, 1.0 equiv) and SnBu2Cl2 (0.15 g, 0.50 mmol, 0.1 equiv) at room temperature. After stirred at room temperature for 5 minutes, the solution was added PhSiH3. The resulting reaction mixture was stirred at 65° C. under N2 for 18 hours, after which the solution was concentrated under vacuum and the residue was purified by silica gel column chromatography EtOAc/heptane, 10-60% to give product (0.7 g). MS: 416 [M+H+].

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 65° C. under N2 for 18 hours
  3. concentrationafter which the solution was concentrated under vacuum
  4. customthe residue was purified by silica gel column chromatography EtOAc/heptane, 10-60%

Sources & evidence

ORD record
ord-2ec190c8054247a1b4deafc0b442adc6
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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