2-(Tributylstannyl)-1,3-thiazole → 2-{4-[3,5-Dimethyl-4-(1,3-thiazol-2-yl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891165Notes

Reaction equation

HRID 891165 reaction equation
I[C:2]1[C:3]([CH3:17])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].C([Sn](CCCC)(CCCC)[C:23]1[S:24][CH:25]=[CH:26][N:27]=1)CCC>C1(C)C=CC=C(C)C=1>[CH3:17][C:3]1[C:2]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[C:6]([CH3:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 222445592-[4-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

Product 1

HCID 222446002-{4-[3,5-Dimethyl-4-(1,3-thiazol-2-yl)-1H-pyrazol-1-yl]phenyl}ethanolYield 5.2%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A mixture of 2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 2 of Example 11) (855 mg, 2.5 mmol), 2-tributylstannylthiazole (3 mmol) and tetrakistriphenylophosphinepalladium (346 mg, 0.3 mol) in m-xylene (6 mL) was refluxed for 16 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 39 mg (5%) of the title compound as yellow oil: MS (EI) m/z 299 [M]+.

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by TLC with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bdb1266f61224233b2b53e0c2f210a95
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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