Stannane, tributyl(1-ethoxyethenyl)- → HCID 68869233, compound

HRID 2105873Notes

Reaction equation

HRID 2105873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23](I)=[CH:22][C:21]=3[O:27][CH2:28][CH3:29])=[N:9]2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]([O:37][CH2:38][CH3:39])=[CH2:36])CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:35]([O:37][CH2:38][CH3:39])=[CH2:36])=[CH:22][C:21]=3[O:27][CH2:28][CH3:29])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68872121HCID 68872121, compound

Product 1

HCID 68869233HCID 68869233, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4,5-Bis-(4-chlorophenyl)-2-(2-ethoxy-4-iodophenyl)-4,5-dihydro-1H-imidazole (0.900 g, 1.68 mmol), tributyl-(1-ethoxyvinyl)tin (0.679 mL, 2.01 mmol) and tetrakis(triphenyl-phosphine)-palladium(0) (0.194 g, 0.168 mmol) were combined in toluene (10 mL) in a flame-dried Schlenk tube then heat at 120° C. for 20 h. After evaporation of volatiles, the residue was purified by flash column chromatography (silica gel, eluting with a gradient of 2-5% methanol in chloroform) to give 4,5-bis-(4-chlorophenyl)-2-[2-ethoxy-4-(1-ethoxyvinyl)phenyl]-4,5-dihydro-1H-imidazole as a faintly green foam (0.639 g, 79%). LC-MS: 481.4 [(M+H)+].

Workup

  1. customAfter evaporation of volatiles
  2. customthe residue was purified by flash column chromatography (silica gel
  3. washeluting with a gradient of 2-5% methanol in chloroform)

Sources & evidence

ORD record
ord-aec6f82dc26f45ac96ec48d7df9445d3
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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