Triphenylphosphine → HCID 123876700、化合物

HRID 712674ノート

反応式

HRID 712674 の反応式
[CH3:1][S:2]([CH2:5][CH:6]=[CH2:7])(=[O:4])=[O:3].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13](Br)[CH:14]=1.CC([O-])=O.[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:7]=[CH:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:14]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 693693,5-DibromopyridineHCID 1400483-Methanesulfonylprop-1-eneHCID 517045Sodium Acetate

生成物 1

HCID 123876700HCID 123876700、化合物収率 36.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

3-Methanesulfonyl-propene (2.4 g, 20 mmol), 3,5-dibromo-pyridine (4.7 g, 20 mmol), NaOAc (1.9 g, 60 mmol), PPh3 (1.6 g, 6.0 mmol) and Pd(OAc)2 (450 mg, 2.0 mmol) are mixed in 1,4-dioxane (350 ml) and heated to reflux for 16 hrs. The reaction mixture is filtered and the filtrate is concentrated. The residue is taken up in DCM and washed with water. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by flash column chromatography to give 2.0 g of 3-bromo-5-(-3-methanesulfonyl-propenyl)-pyridine with some PPh3O.

後処理

  1. temperatureheated
  2. temperatureto reflux for 16 hrs
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. washwashed with water
  6. dry with materialThe organic layer is dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is purified by flash column chromatography

出典と根拠

ORDレコード
ord-833c474a4a0a4adb9b3f78dfc73dae3c
出典データセット
uspto-grants-2015_11
特許番号
US09181272B2

反応ノート

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