Potassium Carbonate → HCID 117601838, compound

HRID 1773754Notes

Reaction equation

HRID 1773754 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][C:13]1[C:17](B2OC(C)(C)C(C)(C)O2)=[C:16]([CH3:27])[O:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][C:13]1[C:17]([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)=[C:16]([CH3:27])[O:15][N:14]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 701324-Bromo-2-nitroanilineHCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol ester

Product 1

HCID 117601838HCID 117601838, compoundYield 93.1%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 4-bromo-2-nitro-phenylamine (150 g, 0.691 mol, 1.0 eq) and 3,5-dimethylisoxazole-4-boronic acid pinacol ester (169 g, 0.725 mol, 1.05 eq) in 1,2-dimethoxyethane (1.5 L) and water (700 mL) were added PdCl2(dppf) (56 g, 69 mmol, 0.1 eq) and K2CO3 (190 g, 1.38 mol, 2.0 eq). The reaction mixture was heated at 95° C. overnight. The reaction mixture was diluted with EtOAc (3 L), washed with brine (2×500 mL). The organic solvent was evaporated and the residue was purified with flash chromatography on silica (PE/EA=10:1-1:1) to give 150 g 4-(3,5-dimethylisoxazol-4-yl)-2-nitroaniline as a red solid.

Workup

  1. washwashed with brine (2×500 mL)
  2. customThe organic solvent was evaporated
  3. customthe residue was purified with flash chromatography on silica (PE/EA=10:1-1:1)

Sources & evidence

ORD record
ord-9ad5b9dbc33746abadb61b8273aa92e7
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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