2-Bromothiazole → HCID 67357223, compound

HRID 884030Notes

Reaction equation

HRID 884030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][CH2:10][C@H:9]2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Br[C:27]1[S:28][CH:29]=[CH:30][N:31]=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH2:10][C@H:9]2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 764302-BromothiazoleHCID 81531DiisopropylethylamineHCID 17998812HCID 17998812, compound

Product 1

HCID 67357223HCID 67357223, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product of Step A in Preparation 17, methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-carboxylate (0.46 g, 1.92 mmol) was dissolved in 1,4-dioxane (2 ml). DIPEA (1.34 ml, 7.67 mmol) and 2-bromo-1,3-thiazole (1.57 g, 9.6 mmol) were added. The reaction was conducted at 180° C. for 20 minutes with microwave. Then, the reaction mixture was concentrated in vacuo. The obtained residue was diluted with EtOAc, washed with water and purified by column chromatography (eluent: EtOAc/Hex=1/3) to give the title compound (0.15 g, 25%).

Workup

  1. concentrationThen, the reaction mixture was concentrated in vacuo
  2. additionThe obtained residue was diluted with EtOAc
  3. washwashed with water
  4. custompurified by column chromatography (eluent: EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-187a197b41494955b58a68f862d8b2d3
Source dataset
uspto-grants-2012_08
Patent number
US08236955B2

Reaction notes

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