Water → HCID 69082460, compound

HRID 594225Notes

Reaction equation

HRID 594225 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([Sn](CCCC)(CCCC)[C:18]1[N:19]=[CH:20][S:21][CH:22]=1)CCC.O.CCOC(C)=O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:21]1[CH:22]=[C:18]([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:19]=[CH:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 143542Ethyl 3-iodobenzoateHCID 27632584-(Tri-n-butylstannyl)thiazole

Product 1

HCID 69082460HCID 69082460, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of commercially available ethyl 3-iodobenzoate (650 mg; 2.35 mmol), 4-(tributylstannyl)thiazole (894 mg; 2.39 mmol), and PdCl2(PPh3)2 (165 mg; 0.23 mmol) in anh. THF (20 ml) was heated to 75° C., under nitrogen, for 17 h. Water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded ethyl 3-(thiazol-4-yl)benzoate as a yellow oil. LC-MS (conditions A): tR=0.78 min.; [M+H]+: 233.94 g/mol.

Workup

  1. extractionThe separated aq. layer was further extracted with AcOEt
  2. washThe mixed organic layers were washed with brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (heptane/AcOEt=1/1)

Sources & evidence

ORD record
ord-0cccdddda3524e7292638b27b085e572
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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