Cesium carbonate → 1-(4-Bromothiazol-2-yl)azetidin-3-ol

HRID 1051698Notes

Reaction equation

HRID 1051698 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.Cl.[NH:9]1[CH2:12][CH:11]([OH:13])[CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:7][C:5]1[N:6]=[C:2]([N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 794004161-(4-Bromothiazol-2-yl)azetidin-3-olYield 55.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-dibromothiazole (1.00 g, 4.12 mmol), azetidin-3-ol hydrochloride (0.543 g, 4.96 mmol), and cesium carbonate (4.03 g, 12.37 mmol) in acetonitrile (30 mL) was stirred for 18 h at 70° C. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum, and the residue was purified via column chromatography on silica gel (eluting with 10:1, dichloromethane/methanol) to afford 1-(4-bromothiazol-2-yl)azetidin-3-ol (0.535 g, 53%) as a light yellow solid. MS (ESI, pos. ion) m/z 235, 237 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was purified via column chromatography on silica gel (eluting with 10:1, dichloromethane/methanol)

Sources & evidence

ORD record
ord-cc75bd6641424b86894ebd89018cd8bc
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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