2-Bromothiazole → Benzyl 2-amino-3-(1,3-thiazol-2-ylethynyl)benzoate

HRID 1851408Notes

Reaction equation

HRID 1851408 reaction equation
[NH2:1][C:2]1[C:17]([C:18]#[CH:19])=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].Br[C:21]1[S:22][CH:23]=[CH:24][N:25]=1>C(N(CC)CC)C.C(OCC)(=O)C.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.[Cu](I)I>[NH2:1][C:2]1[C:17]([C:18]#[C:19][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

7

Reactant 2

HCID 764302-BromothiazoleHCID 57901749Benzyl 2-amino-3-ethynylbenzoate

Product 1

HCID 57901686Benzyl 2-amino-3-(1,3-thiazol-2-ylethynyl)benzoateYield 82%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 2-amino-3-ethynylbenzoate (3.06 g), 2-bromothiazole (1.65 mL), bis(triphenylphosphine)palladium(II) dichloride (0.704 g) and copper iodide (0.232 g) in triethylamine (60 mL) was stirred under a nitrogen atmosphere at 60° C. for 1.5 hr with heating. The reaction mixture was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50) to give the title compound (3.32 g, yield 82%) as a yellow oil.

Workup

  1. temperaturewith heating
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50)

Sources & evidence

ORD record
ord-630f7093ad7b485996d9b57e4524f054
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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