Hexamethylditin → 2-Acetoxymethyl-4-(trimethylstannyl)thiazole

HRID 2306284Notes

Reaction equation

HRID 2306284 reaction equation
[C:1]([O:4][CH2:5][C:6]1[S:7][CH:8]=[C:9](Br)[N:10]=1)(=[O:3])[CH3:2].C[Sn](C)C.C[Sn](C)C.N1(C2SC=[C:29]([Sn:31](C)([CH3:33])[CH3:32])N=2)CCCCC1>C1(C)C=CC=CC=1.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>[C:1]([O:4][CH2:5][C:6]1[S:7][CH:8]=[C:9]([Sn:31]([CH3:33])([CH3:32])[CH3:29])[N:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6327618HexamethylditinHCID 187616162-Acetoxymethyl-4-bromothiazoleHCID 591182862-Piperidinyl(trimethylstannyl)thiazole

Product 1

HCID 187616032-Acetoxymethyl-4-(trimethylstannyl)thiazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-Acetoxymethyl-4-bromothiazole (387) was taken up in degassed toluene (0.1 M), and was then treated hexamethylditin (10 equiv) and tetrakis(triphenylphosphine)palladium(0) (0.1 equiv) at 80° C. for 3 h according to the procedure described for the synthesis of 2-piperidinyl-4-(trimethylstannyl)thiazole (373), to yield, after flash column chromatography (silica gel, 5% NEt, in hexanes), 2-dacetoxymethyl-4-(trimethylstannyl)thiazole (388; 100%).

Workup

  1. customto yield

Sources & evidence

ORD record
ord-b7e3ceff3620405aa946bbfd4175438a
Source dataset
uspto-grants-2002_08
Patent number
US06441186B1

Reaction notes

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