Water → HCID 74435704, compound

HRID 1963020Notes

Reaction equation

HRID 1963020 reaction equation
Br[C:2]1[N:3]=[C:4]([CH2:7][O:8][C:9]2[C:10]([F:20])=[C:11]([C:16]([F:19])=[CH:17][CH:18]=2)[C:12](=[N:14][OH:15])[NH2:13])[S:5][CH:6]=1.[CH3:21][O:22][C:23]1[S:24][C:25]([Sn](CCCC)(CCCC)CCCC)=[CH:26][N:27]=1.O>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:20][C:10]1[C:9]([O:8][CH2:7][C:4]2[S:5][CH:6]=[C:2]([C:25]3[S:24][C:23]([O:22][CH3:21])=[N:27][CH:26]=3)[N:3]=2)=[CH:18][CH:17]=[C:16]([F:19])[C:11]=1[C:12](=[N:14][OH:15])[NH2:13]

Participants

6

Reactant 3

HCID 962WaterHCID 164271192-Methoxy-5-(tributylstannyl)-1,3-thiazoleHCID 72334040HCID 72334040, compound

Product 1

HCID 74435704HCID 74435704, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-((4-bronnothiazol-2-yl)methoxy)-2,6-difluoro-N′-hydroxy benzimidamide (0.20 g, 0.55 mmol) in DMF (4.0 ml) was added 2-methoxy-5-(tributylstannyl)thiazole (0.23 g, 0.55 mmol) and the resulting reaction mixture was purged with nitrogen for 15 min. Tetrakis(triphenylphosphine) palladium (0) (0.06 g, 0.05 mmol) was then added and the reaction mixture was heated at 100° C. for 3 h under the nitrogen atmosphere. The reaction mixture was then cooled to room temperature, added water (25 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The compound was purified by column chromatography on silica (60-120 M, 35% EtOAc-Hexane) yielding the title compound as white solid (0.06 g, 27%).

Workup

  1. customthe resulting reaction mixture
  2. customwas purged with nitrogen for 15 min
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated to dryness under reduced pressure
  7. customThe compound was purified by column chromatography on silica (60-120 M, 35% EtOAc-Hexane)

Sources & evidence

ORD record
ord-13e6520e45614e4e861b0137005dd92c
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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