4-Aminocarbonylphenylboronic acid → 4-(4-Nitroisothiazol-5-yl)benzamide

HRID 871041Notes

Reaction equation

HRID 871041 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Br[C:14]1[S:18][N:17]=[CH:16][C:15]=1[N+:19]([O-:21])=[O:20].C([O-])(O)=O.[Na+].O>O1CCOCC1.C(OCC)(=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[N+:19]([C:15]1[CH:16]=[N:17][S:18][C:14]=1[C:7]1[CH:8]=[CH:9][C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=1)([O-:21])=[O:20]

Participants

7

Reactant 3

HCID 27378114-Aminocarbonylphenylboronic acidHCID 126311735-Bromo-4-nitroisothiazoleHCID 86585896Sodium bicarbonate water

Product 1

HCID 867208594-(4-Nitroisothiazol-5-yl)benzamideYield 10,000%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-carbamoylphenylboronic acid (3Q) (157 mg, 0.96 mmol) and 5-bromo-4-nitroisothiazole (P) (200 mg, 0.96 mmol) in dioxane was bubbled was nitrogen gas for 5 min Bis(tri-tert-butylphosphine)palladium (0) (49 mg, 0.096 mmol) and 1.2M NaHCO3 water solution (241 mg, 2.9 mmol) was added and stirred at 120° C. under nitrogen atmosphere for 15 min The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water, and concentrated in vacuo at room temperature (25° C.) to afford the product 4-(4-nitroisothiazol-5-yl)benzamide (3C4) (250 mg, 96 mmol)

Workup

  1. customfor 5 min
  2. additionwas added
  3. temperaturewas cooled to room temperature
  4. washwashed with water
  5. concentrationconcentrated in vacuo at room temperature (25° C.)

Sources & evidence

ORD record
ord-9978678324104fb6972525ecd7461f0b
Source dataset
uspto-grants-2015_03
Patent number
US08969584B2

Reaction notes

Loading…