Sodium Carbonate → 1,3-Bis(1,1-dimethylethyl) 2-(4'-cyano-5,2'-dimethyl[1,1'-biphenyl]-3-yl)propanedioate

HRID 341127노트

반응식

HRID 341127 반응식
I[C:2]1[CH:3]=[C:4]([CH:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[C:28]([CH3:35])[CH:27]=1)#[N:25].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH:3]=2)=[C:28]([CH3:35])[CH:27]=1)#[N:25]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 16218401(4-Cyano-2-methyl-phenyl)boronic acidHCID 682821791,3-Bis(1,1-dimethylethyl) 2-(3-iodo-5-methylphenyl)propanedioate2회

생성물 1

HCID 682824311,3-Bis(1,1-dimethylethyl) 2-(4'-cyano-5,2'-dimethyl[1,1'-biphenyl]-3-yl)propanedioate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

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온도
80 °C

실험 절차

A mixture of 1,3-bis(1,1-dimethylethyl) 2-(3-iodo-5-methylphenyl)propanedioate (the product of Step A, 320 mg, 0.74 mmol), 4-cyano-2-methylphenylboronic acid (178 mg, 1.11 mmol), sodium carbonate (78 mg, 0.74 mmol), bis(triphenylphosphine)palladium(II) dichloride (52 mg, 0.074 mmol), dioxane (5 mL), and water (1 mL) was heated to 80° C. and stirred for 20 minutes. The reaction mixture was then cooled to room temperature, and filtered through a plug of silica gel eluting with 20% ethyl acetate in hexanes. Concentration of the eluant under reduced pressure provided a brown oil (430 mg) containing the crude product, which was used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationfiltered through a plug of silica gel eluting with 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-190c29f2a4be487bbcc6f201817819a7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895738B2

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