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

HRID 57812

反応式

HRID 57812 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-09526792083b4bb8a99e50999cd69c27
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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