2-(Tri-n-butylstannyl)oxazole → HCID 10154809, compound

HRID 586338Notes

Reaction equation

HRID 586338 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.C([Sn](CCCC)(CCCC)[C:34]1[O:35][CH:36]=[CH:37][N:38]=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.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:19])([F:18])[F:20])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:34]1[O:35][CH:36]=[CH:37][N:38]=1

Participants

6

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 57438077HCID 57438077, compound

Product 1

HCID 10154809HCID 10154809, compoundYield 35.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of trifluoromethanesulfonic acid 2-fluoro-5-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)phenyl ester (45 mg, 0.104 mmol), 2-(tributylstannyl)oxazole (70 mg, 0.196 mmol), tetrakis(triphenylphosphine)palladium(0) (30 mg, 0.026 mmol) and copper(I) iodide (15 mg, 0.079 mmol) in 1,4-dioxane (4 ml) was heated at 170° C. for 30 min using a Smith Synthesizer microwave apparatus. The mixture was evaporated in vacuo and the residue was purified by chromatography (silica gel, 8% Et2O/CH2Cl2), followed by trituration with diethyl ether, to give 13 mg (35%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 7.37 (1H, s), 7.42 (1H, dd, J 8.7, 10.2 Hz), 7.85 (1H, s), 8.19 (1H, ddd, J 8.8, 4.6, 2.4 Hz), 8.66 (1H, s), 8.82 (1H, dd, J 9.1, 2.4 Hz), 8.86 (1H, s); MS (ES+) m/z 350.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by chromatography (silica gel, 8% Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-26ce30bb19cf4d38b1a519e1ff84182b
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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