4-(Tri-n-butylstannyl)thiazole → HCID 86649430, compound

HRID 2098213Notes

Reaction equation

HRID 2098213 reaction equation
Br[C:2]1[N:3]=[CH:4][S:5][C:6]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C([Sn](CCCC)(CCCC)[C:20]1[N:21]=[CH:22][S:23][CH:24]=1)CCC>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>[S:5]1[C:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:2]([C:20]2[N:21]=[CH:22][S:23][CH:24]=2)[N:3]=[CH:4]1

Participants

5

Reactant 2

HCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 687870291239464-76-6

Product 1

HCID 86649430HCID 86649430, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of tert-butyl 4-bromothiazol-5-ylcarbamate (590 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (240 mg, 0.21 mmol) and 4-tributylstannylthiazole (1.18 g, 3.2 mmol) in anhydrous dioxane (5 mL) was heated to 140° C. in a microwave reactor for 1 h. The reaction mixture was then concentrated in vacuo and purified by flash chromatography (EtOAc/hexanes elution) to give the desired product (420 mg, 71%). MH+ 283.9.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified by flash chromatography (EtOAc/hexanes elution)

Sources & evidence

ORD record
ord-60cd6604d36b41c59421d5ea4546e3be
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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