Sodium Carbonate → 3-Bromo-5-thiophen-3-yl-pyridine

HRID 1385993ノート

反応式

HRID 1385993 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[S:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:11]2[CH:12]=[CH:13][S:9][CH:10]=2)[CH:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 581760Thiophene-3-boronic acid

生成物 1

HCID 112764923-Bromo-5-thiophen-3-yl-pyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A deoxygenated solution of 3,5-dibromopyridine (4.00 g, 16.9 mmol, 1 equiv), 3-thiopheneboronic acid (2.38 g, 18.6 mmol, 1.10 equiv), Pd(PPh3)4 (781 mg, 0.676 mmol, 0.0433 equiv), and 2.0 M Na2CO3 (16.9 mL, 33.8 mmol, 2.00 equiv) in dioxane (40 ml) was heated under argon at reflux for 20 h. The reaction mixture was allowed to cool, then partitioned between water (200 mL) and ethyl acetate (2×300 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (5% ethyl acetate in dichloromethane) to afford 3-bromo-5-thiophen-3-yl-pyridine as a white solid.

後処理

  1. temperatureat reflux for 20 h
  2. temperatureto cool
  3. custompartitioned between water (200 mL) and ethyl acetate (2×300 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (5% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-894d7d9f6cbf461b80a5bbec4d00673a
出典データセット
uspto-grants-2001_07
特許番号
US06265403B1

反応ノート

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