Sodium Carbonate → HCID 90462335, compound

HRID 588876Notes

Reaction equation

HRID 588876 reaction equation
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)=[O:8].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][N:9]([C:7]([C:6]2[C:5]([O:23][CH3:24])=[CH:4][C:3]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:2]([Cl:1])[CH:22]=2)=[O:8])[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 46481146HCID 46481146, compound

Product 1

HCID 90462335HCID 90462335, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(5-chloro-4-iodo-2-methoxybenzoyl)piperazine-1-carboxylate (300 mg, 0.56 mmol), phenylboronic acid (82 mg, 0.67 mmol), Pd(PPh3)4 (129 mg, 0.1 mmol), Na2CO3 (180 mg, 1.68 mmol) in 1,4-dioxane (10 mL) and water (2 mL) was stirred at reflux under argon for 16 h. The mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1) to afford the desired product (219 mg, 80% yield).

Workup

  1. temperatureat reflux under argon for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1)

Sources & evidence

ORD record
ord-5d84ab797bcf462f9470afeedd75bb6c
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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