Triphenylphosphine → HCID 123876700, 화합물

HRID 712674노트

반응식

HRID 712674 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 123876700HCID 123876700, 화합물수율 36.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-833c474a4a0a4adb9b3f78dfc73dae3c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181272B2

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