Sodium Carbonate → 5-Chloro-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

HRID 1846040Notes

Reaction equation

HRID 1846040 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([O:21][CH3:22])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].Br[C:24]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].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>[Cl:32][C:30]1[CH:31]=[C:24]([C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[O:21][CH3:22])[C:25]([C:26]#[N:27])=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 234985242-Bromo-4-chlorobenzonitrileHCID 867232082-(4-(Ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 867232635-Chloro-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-carbonitrileYield 62%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 542 mg, 1.66 mmol) in dioxane (10 mL) and water (2 mL) was added 2-bromo-4-chlorobenzonitrile (300 mg, 1.38 mmol), and sodium carbonate (441 mg, 4.16 mmol). The reaction was degassed and then tetrakis(triphenylphosphine)palladium(0) (160 mg, 0.14 mmol) was added and the reaction mixture further degassed. The reaction was on a preheated hot plate (110° C.) for 16 hours. The reaction mixture was cooled to room temperature and filtered through celite and the solvent removed in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc:cyclohexane 1:1 to give the title compound as a dark solid in 62% yield, 0.345 g.

Workup

  1. customThe reaction was degassed
  2. filtrationfiltered through celite
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with EtOAc:cyclohexane 1:1

Sources & evidence

ORD record
ord-281cf03607ab45be8cec12ced6e312af
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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