Water → HCID 69084075, compound

HRID 594234Notes

Reaction equation

HRID 594234 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[S:18][CH:19]=[CH:20][N:21]=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:18]1[CH:19]=[CH:20][N:21]=[C:17]1[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 16217886Methyl 6-bromopyridine-2-carboxylate

Product 1

HCID 69084075HCID 69084075, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of commercially available methyl 6-bromopicolinate (300 mg; 1.38 mmol), 2-(tributylstannyl)thiazole (623 mg; 1.66 mmol), and PdCl2(PPh3)2 (97 mg; 0.13 mmol) in anh. THF (8 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 methyl 6-(thiazol-2-yl)picolinate as a pale yellow solid. LC-MS (conditions A): tR=0.60 min.; [M+H]+: 220.95 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-f7bbf7e9a7f34d7eb2f18f42b3d9a877
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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