Sodium Carbonate → N,N-Dimethyl-6-((E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)naphthalen-2-amine

HRID 641813노트

반응식

HRID 641813 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:12]([CH3:14])[CH3:13])[CH:6]=[CH:5]2.[CH3:15][C:16]1[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([CH3:23])=[CH:19][C:20]=1[CH:21]=[CH2:22].C([O-])([O-])=O.[Na+].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH3:13][N:12]([CH3:14])[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:22]=[CH:21]/[C:20]3[CH:19]=[C:18]([CH3:23])[N:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]=3[CH3:15])[CH:3]=2)[CH:8]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 155089076-bromo-N,N-dimethylnaphthalen-2-amineHCID 592592882,5-Dimethyl-1-phenyl-3-vinyl-1H-pyrrole

생성물 1

HCID 59259285N,N-Dimethyl-6-((E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)naphthalen-2-amine수율 17.1%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Dry DMF (10 mL) was added by syringe to the mixture of 6-bromo-N,N-dimethylnaphthalen-2-amine (200 mg, 0.8 mmol), 2,5-dimethyl-1-phenyl-3-vinyl-1H-pyrrole (236 mg, 1.2 mmol), Na2CO3 (254 mg, 2.4 mmol), n-Bu4NCl (224 mg, 0.8 mmol) and Pd(OAc)2 (8 mg, 0.33 mmol). The reaction mixture was stirred at 100° C. for 3 hrs, then quenched with water (20 mL) and extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous Na2SO4. After purified by column chromatography (hexane/EtOAc=500:1), the target compound was obtained as brown yellow solid (50 mg, 17%). MS [M+]=366, LC-MS: tR=3.28 min.

후처리

  1. customquenched with water (20 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter purified by column chromatography (hexane/EtOAc=500:1)

출처 및 근거

ORD 기록
ord-26113b85d03d45cb9a16f6db045972a0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696227B2

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