4-(Tri-n-butylstannyl)thiazole → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-methanesulfonyl-5-thiazol-4-yl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl Ester

HRID 418068Notes

Reaction equation

HRID 418068 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24](I)[CH:23]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:2].C([Sn](CCCC)(CCCC)[C:46]1[N:47]=[CH:48][S:49][CH:50]=1)CCC>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:46]3[N:47]=[CH:48][S:49][CH:50]=3)[CH:25]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:27]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:2]

Participants

6

Reactant 2

HCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 578630374-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl Ester

Product 1

HCID 578631244-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-methanesulfonyl-5-thiazol-4-yl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl EsterYield 99.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (300 mg, 0.436 mmol) in toluene (20 mL), 4-(tributylstannyl)thiazole (243 mg, 0.25 mL, 0.653 mmol) was added, followed by Pd(PPh3)4 (25 mg, 0.0217 mmol). The reaction mixture was heated at 90° C. overnight. The reaction was diluted with EtOAc (250 mL), washed with water (100 mL). The organic layer was washed with brine, dried over Na2SO4, concentration under reduced pressure gave an oil which was purified by column chromatography. The title compound was eluted with 50% EtOAc/Hexanes to provide title compound (280 mg, 99%) as an oil.

Workup

  1. washwashed with water (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4, concentration under reduced pressure
  4. customgave an oil which
  5. customwas purified by column chromatography
  6. washThe title compound was eluted with 50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-da53e99a29df4164ab342fb8a7d83e54
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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