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Triethylamine → 3-Ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

HRID 249737
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HRID 249737 반응식
Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([O:10][CH3:11])=[C:6]([CH2:8][CH3:9])[CH:7]=1.[CH3:13][C:14]1([CH3:21])[C:18]([CH3:20])([CH3:19])[O:17][BH:16][O:15]1.C(N(CC)CC)C>O1CCOCC1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:8]([C:6]1[C:5]([O:10][CH3:11])=[N:4][C:3]([CH3:12])=[C:2]([B:16]2[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:21])([CH3:13])[O:15]2)[CH:7]=1)[CH3:9]
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 116586693-Bromo-5-ethyl-6-methoxy-2-methylpyridine

생성물 1

HCID 574164103-Ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine수율 72%

시약·촉매·용매 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

3-Bromo-5-ethyl-6-methoxy-2-methylpyridine (11.51 g, 50 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.31 g, 64.95 mmol) and triethylamine (21.84 ml, 164.4 mmol) were dissolved under argon in 100 ml of dioxane and then 1,1′bis(diphenylphosphino)ferrocenepalladium(II) chloride (1.94 g, 2.65 mmol) was added. The mixture was stirred at 90° C. for 18 h, cooled and diluted with ethyl acetate, and filtered through silica gel. The solution was cooled to 0° C., mixed with water and extracted twice with ethyl acetate. The dried and concentrated organic phase was chromatographed on silica gel dried at 45° C. in a vacuum drying oven. A pale beige solid (9.94 g, 72%) was obtained.

후처리

  1. temperaturecooled
  2. filtrationfiltered through silica gel
  3. temperatureThe solution was cooled to 0° C.
  4. additionmixed with water
  5. extractionextracted twice with ethyl acetate
  6. customThe dried
  7. customconcentrated organic phase was chromatographed on silica gel
  8. customdried at 45° C. in a vacuum
  9. customdrying oven

출처 및 근거

ORD 기록
ord-29f3a7413a844905837944ddd07df9aa
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863280B2

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