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tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 5-(1,3-thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 490220
Notes
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Reaction equation

HRID 490220 reaction equation
[Br-].[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Zn+].FC(F)(F)S(O[C:14]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][CH2:16][CH:15]=1)(=O)=O>O1CCCC1>[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:16]1[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:14][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 53978067tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateHCID 178419763HCID 178419763, compound

Product 1

HCID 57440157tert-butyl 5-(1,3-thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To the mixture of 2-thiazolylzinc bromide (20 mL, 10 mmol) in dry tetrahydrofuran (30 mL) at 0° C. was added the product from Example 328B (3.3 gm, 10 mmol) and tetrakis(tripehynlphosphine) palladium (0) (10% mole 1.1 g). The mixture was heated at 50° C. for 1 hour, cooled to room temperature, quenched with brine and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 25% ethyl acetate:hexanes) to obtain desired product 1.4 g (60%) as colorless oil. MS (DCI/NH3) m/e 265 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, 25% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-e24430c2f5b0478ebe16d2baf030804a
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528134B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes