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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
ノート
印刷プレビュー

反応式

HRID 249737 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-29f3a7413a844905837944ddd07df9aa
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07863280B2

反応ノート

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