3,5-Dibromopyridine → 3-Bromo-5-(prop-1-en-2-yl)pyridine

HRID 57812

반응식

HRID 57812 반응식
O.C([O-])(=O)C.[K+].O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Br:30])[CH:29]=1.[C:31](B1OC(C)(C)C(C)(C)O1)([CH3:33])=[CH2:32]>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].ClCCl.C(#N)C>[Br:30][C:28]1[CH:27]=[N:26][CH:25]=[C:24]([C:31]([CH3:33])=[CH2:32])[CH:29]=1

참가 물질

7

반응물 4

HCID 693693,5-DibromopyridineHCID 151402Sodium Carbonate DecahydrateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 23702041Potassium acetate hydrate

생성물 1

HCID 234368083-Bromo-5-(prop-1-en-2-yl)pyridine수율 52%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct; 98.0 mass %, potassium acetate hydrate (7.4997 mmol; 3.7 mL), sodium carbonate decahydrate (7.4997 mmol; 3.7 mL), Acetonitrile (15 mL) and 3,5-dibromopyridine (4.9998 mmol; 1184.4 mg) in 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.9998 mmol; 840.0 mg; 0.940 mL) in a pressure tube was heated under microwave at 120° C. for 3 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer was concentrated. The residue was purified on silica eluted with 0 to 10% MeOH in DCM to afford 3-bromo-5-isopropenyl-pyridine as a dark tan solid (512.6 mg, 52%).

후처리

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. concentrationThe combined organic layer was concentrated
  4. customThe residue was purified on silica
  5. washeluted with 0 to 10% MeOH in DCM

출처 및 근거

ORD 기록
ord-09526792083b4bb8a99e50999cd69c27
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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