Hydrochloric Acid → HCID 178514822, compound

HRID 746477Notes

Reaction equation

HRID 746477 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.C([O:17][B:18]([CH:24]=[CH2:25])OCCCC)CCC.Cl>C1COCC1.O>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[CH:25]=[CH:24][BH:18][OH:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 122863-BromopyridineHCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 178418918HCID 178418918, compound

Product 1

HCID 178514822HCID 178514822, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromopyridine (1.60 g, 10.0 mmol) in THF (15 mL) was added isopropylmagnesium chloride (2.0 M in THF) (5.0 mL, 10 mmol) under nitrogen atmosphere at room temperature, and the mixture was stirred for 1 h. To the mixture was added vinylboronic acid dibutyl ester (3.4 mL) drop wise, and the mixture was stirred at room temperature for 18 h. Water was added and the pH was adjusted to 7 with 1 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound (1.04 g, 78%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8a3917500d0d4bab82b27e8e8907ecc0
Source dataset
uspto-grants-2008_07
Patent number
US07393856B2

Reaction notes

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