2-(Tributylstannyl)-1,3-thiazole → HCID 23077540, compound

HRID 1349510Notes

Reaction equation

HRID 1349510 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13](Br)=[CH:12][O:11][C:10]=1[C:17]([O:19][CH3:20])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[Sn](CCCC)(CCCC)CCCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([C:22]2[S:21][CH:25]=[CH:24][N:23]=2)=[CH:12][O:11][C:10]=1[C:17]([O:19][CH3:20])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 22937753HCID 22937753, compound

Product 1

HCID 23077540HCID 23077540, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3-benzyloxy-5-bromo-4-oxo-4H-pyran-2-carboxylate (2.3 g) in dioxane (25 ml) were added tetrakis(triphenylphosphine)palladium(0) (1.57 g) and (2-thiazolyl)tributyltin (5.08 g) under an argon stream, and the mixture was stirred at 100° C. for 1.5 hr. The obtained reaction mixture was concentrated, and subsequently purified by silica gel column chromatography (ethyl acetate:hexane=1:4–1:2) to give methyl 3-benzyloxy-4-oxo-5-(thiazol-2-yl)-4H-pyran-2-carboxylate (1.47 g).

Workup

  1. customThe obtained reaction mixture
  2. concentrationwas concentrated
  3. customsubsequently purified by silica gel column chromatography (ethyl acetate:hexane=1:4–1:2)

Sources & evidence

ORD record
ord-18aa9e8a927643749dc830c191ae2fc9
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

Loading…