Potassium Carbonate → HCID 86691765, compound

HRID 2172415Notes

Reaction equation

HRID 2172415 reaction equation
[CH:1]1([N:7]2[C:20](=[O:21])[C:18]3=[C:19]4[C:14](=[CH:15][CH:16]=[CH:17]3)[C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][CH:11]=[C:10]4[C:8]2=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=1[N+:39]([O-:41])=[O:40].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(O)C>[CH:1]1([N:7]2[C:20](=[O:21])[C:18]3=[C:19]4[C:14](=[CH:15][CH:16]=[CH:17]3)[C:13]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[N+:39]([O-:41])=[O:40])=[CH:12][CH:11]=[C:10]4[C:8]2=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzeneHCID 86691766HCID 86691766, compound

Product 1

HCID 86691765HCID 86691765, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a Schlenk tube, 2 g of N-cyclohexyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-naphthalene-1,8-dicarboximide (4.93 mmol), 1.75 g of 1-bromo-4-chloro-2-nitrobenzene (7.40 mmol) were dissolved in 80 mL of toluene, 1.6 g of potassium carbonate (11.6 mmol) in 8 mL of water and 0.8 mL of ethanol are added, and the mixture was thoroughly degassed. After addition of 800 mg of tetrakis(triphenyl-phosphine)palladium(0) (0.717 mmol), the mixture was degassed again and stirred at 80° C. under argon for 2 days.

Workup

  1. customthe mixture was thoroughly degassed
  2. customthe mixture was degassed again

Sources & evidence

ORD record
ord-e62c2f995aed49d09bc787cd8cfd8d70
Source dataset
uspto-grants-2015_06
Patent number
US09054325B2

Reaction notes

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