Potassium Carbonate → HCID 28819282, compound

HRID 1888145Notes

Reaction equation

HRID 1888145 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[C:10]1[S:11][CH:12]=[CH:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[S:11]1[CH:12]=[CH:13][N:14]=[C:10]1[N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 145742L-Proline

Product 1

HCID 28819282HCID 28819282, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 80 mg (0.70 mmol) of L-Proline in 3 mL of anhydrous N,N-dimethylformamide at ambient temperature was added 0.062 ml (0.70 mmol) of 2-bromothiazole, 288 mg (2.09 mmol) of potassium carbonate, and 13 mg (0.068 mmol) of copper(I)iodide. The reaction mixture was heated to 100° C. overnight then filtered through a plug of Celite®. The crude residue was purified by reverse-phase HPLC (TMC Pro-Pac C18; 0-60% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to give the title compound as a light brown solid. (0.065 g, 50%). LC-MS: m/z (ES) 199.2 (MH)+.

Workup

  1. filtrationthen filtered through a plug of Celite®
  2. customThe crude residue was purified by reverse-phase HPLC (TMC Pro-Pac C18; 0-60% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)

Sources & evidence

ORD record
ord-fc5fbabdeeb34a638d5773e4b1962f14
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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