Potassium Carbonate → 4-(6-Chlorobenzo[c][1,2,5]oxadiazol-5-yl)aniline

HRID 407114Notes

Reaction equation

HRID 407114 reaction equation
Br[C:2]1[C:10]([Cl:11])=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1.B([O-])[O-].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(#N)C.O.ClCCl>[Cl:11][C:10]1[C:2]([C:2]2[CH:10]=[CH:9][C:5]([NH2:6])=[CH:4][CH:3]=2)=[CH:3][C:4]2[C:5]([CH:9]=1)=[N:6][O:7][N:8]=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 674684685-Bromo-6-chlorobenzo[c][1,2,5]oxadiazoleHCID 178514824HCID 178514824, compound

Product 1

HCID 674679184-(6-Chlorobenzo[c][1,2,5]oxadiazol-5-yl)anilineYield 44.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 67448433Dioxane acetonitrile waterSolvent

Conditions

Temperature
95 °C

Procedure

Palladium tetrakis-triphenylphosphine (37 mg, 32 μmol) was added to a degassed solution of bromide 94 (150 mg, 643 μmol) and boronate 84 (211 mg, 964 μmol) in dioxane:acetonitrile:water (9:9:2, 3.2 mL) and potassium carbonate (205 mg, 964 μmol). The resulting mixture was heated under argon at 95° C. with stirring for 1 h. The mixture was then cooled, diluted with dichloromethane (25 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 95 (35 mg, 22%) as a solid: LRESIMS m/z 246.0 [M+H]+, calcd. for C12H9Cl1N3O1 246.0.

Workup

  1. temperatureThe mixture was then cooled
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18358ffb94074c7fa96d34b6223685da
Source dataset
uspto-grants-2014_06
Patent number
US08754219B2

Reaction notes

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