Water → HCID 86631780, compound

HRID 2048149Notes

Reaction equation

HRID 2048149 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C([Sn](CCCC)(CCCC)[C:24]1[S:25][CH:26]=[CH:27][N:28]=1)CCC.O>O1CCOCC1>[S:25]1[CH:26]=[CH:27][N:28]=[C:24]1[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 86631781HCID 86631781, compound

Product 1

HCID 86631780HCID 86631780, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

0.5 g (1.65 mM) 4-(3-bromoimidazo[1,2-a]pyrimidin-2-yl)benzaldehyde is dissolved in 15 mL of 1,4-Dioxane. To this solution is added tetrakis triphenylphosphine palladium (200 mg) 40%. The reaction mixture is heated at 100° C. for 10 min. and 2-(tributylstannyl)-1,3-thiazole is added (681 mg, 1.81 mM). The reaction is heated (oil bath or microwave) at same temp for 5 h. The reaction is cooled to room temperature and 50 mL of water is added and the reaction mixture is extracted with ethyl acetate. The organic layer is dried and concentrated. The crude is purified by flash column chromatography to yield the desired product.

Workup

  1. temperatureThe reaction is heated (oil bath or microwave) at same temp for 5 h
  2. temperatureThe reaction is cooled to room temperature
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customThe crude is purified by flash column chromatography

Sources & evidence

ORD record
ord-c299c79795864a08b409c222ea668b38
Source dataset
uspto-grants-2013_11
Patent number
US08592591B2

Reaction notes

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