Water → HCID 69085658, compound

HRID 594228Notes

Reaction equation

HRID 594228 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[S:22][CH:21]=[N:20][CH:19]=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:22]1[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])=[CH:19][N:20]=[CH:21]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 143542Ethyl 3-iodobenzoateHCID 27632575-(Tributylstannyl)-1,3-thiazole

Product 1

HCID 69085658HCID 69085658, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of commercially available ethyl 3-iodobenzoate (1.000 g; 3.62 mmol), 5-(tributylstannyl)thiazole (1.355 g; 3.62 mmol), and PdCl2(PPh3)2 (254 mg; 0.36 mmol) in anh. THF (20 ml) was heated to 75° C., under nitrogen, for 18 h. After cooling to rt, 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-5-yl)benzoate as a pale yellow solid. LC-MS (conditions A): tR=0.75 min.; [M+H]+: 233.94 g/mol.

Workup

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

Sources & evidence

ORD record
ord-112f89d6ae76408889ac98e8082bce8b
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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