Cesium fluoride → 2',6'-Bis(2,2,6,6-tetramethylpiperidin-1-yl)-2,3'-bipyridine

HRID 1779137노트

반응식

HRID 1779137 반응식
Br[C:2]1[C:3]([N:18]2[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]2([CH3:27])[CH3:26])=[N:4][C:5]([N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][CH2:10][C:9]2([CH3:17])[CH3:16])=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)CCC.[F-].[Cs+]>C1(C)C=CC=CC=1.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>[CH3:27][C:19]1([CH3:26])[CH2:20][CH2:21][CH2:22][C:23]([CH3:25])([CH3:24])[N:18]1[C:3]1[C:2]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:7][CH:6]=[C:5]([N:8]2[C:9]([CH3:16])([CH3:17])[CH2:10][CH2:11][CH2:12][C:13]2([CH3:15])[CH3:14])[N:4]=1

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 676092893-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine

생성물 1

HCID 678921422',6'-Bis(2,2,6,6-tetramethylpiperidin-1-yl)-2,3'-bipyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of 3-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine (0.4 g, 0.92 mmol), 2-(tributylstannyl)pyridine (0.4 g, 1.10 mmol), Pd(PPh3)4 (0.053 g, 0.046 mmol), and Cesium fluoride (0.28 g, 1.83 mmol) in Toluene (30 ml) was stirred under reflux for 2 days. After cooling down to room temperature the reaction was quenched with saturated CsF aqueous solution (100 mL). The product was extracted with ethylacetate. The product was purified by column chromatography on silica gel and obtained as white solide (Rf=0.5 in Ethylacetate:hexane=1:4, Yield=50 mg (12.5%))

후처리

  1. temperatureunder reflux for 2 days
  2. customwas quenched with saturated CsF aqueous solution (100 mL)
  3. extractionThe product was extracted with ethylacetate
  4. customThe product was purified by column chromatography on silica gel
  5. customobtained as white solide (Rf=0.5 in Ethylacetate:hexane=1:4, Yield=50 mg (12.5%))

출처 및 근거

ORD 기록
ord-f26caf7e0acf4eb181c046c258d077f3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09269912B2

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