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Toluene → 2-(3-Methyl-2,2'-bipyridin-6-yl)isoindoline-1,3-dione

HRID 1890742
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HRID 1890742 반응식
Br[C:2]1[N:7]=[C:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:5]=[CH:4][C:3]=1[CH3:19].C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)CCC.C1(C)C=CC=CC=1>C(OCC)(=O)C.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>[CH3:19][C:3]1[C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:7][C:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:5][CH:4]=1
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참가 물질

6

반응물 3

HCID 1140TolueneHCID 6077842-(Tributylstannyl)pyridineHCID 583179502-(6-Bromo-5-methylpyridin-2-yl)isoindoline-1,3-dione

생성물 1

HCID 583179152-(3-Methyl-2,2'-bipyridin-6-yl)isoindoline-1,3-dione

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 8857
Ethyl Acetate
용매

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온도
116 °C

실험 절차

To a reaction vessel under argon containing 2-(6-bromo-5-methylpyridin-2-yl)isoindoline-1,3-dione (85 mg, 0.27 mmol), 2-(tributylstannyl)pyridine (123 mg, 0.32 mmol), Pd(PPh3)4(31 mg, 0.027 mmol) is added anhydrous toluene (0.7 ml). The mixture is heated to 116° C. with an oil bath for 18 hours, cooled to room temperature, diluted with ethyl acetate and filtered through a celite pad to remove any solids. The filtrate is concentrated to afford 2-(3-methyl-2,2′-bipyridin-6-yl)isoindoline-1,3-dione as a brown solid (LC-MS m/z: 316.1 (M+1)) which is used without further purification in the next step.

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a celite pad
  3. customto remove any solids
  4. concentrationThe filtrate is concentrated

출처 및 근거

ORD 기록
ord-ec59e03480a847b6aa8065580ac7160c
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08507491B2

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