Hydrochloric Acid → HCID 178514823, compound

HRID 1364191Notes

Reaction equation

HRID 1364191 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.C([O:17][B:18]([CH:24]=[CH2:25])OCCCC)CCC.Cl>C1COCC1.O>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH:25]=[CH:24][BH:18][OH:17])[CH:8]=1

Participants

7

Reactant 4

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

Product 1

HCID 178514823HCID 178514823, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isopropylmagnesium chloride (2.0 M in THF) (5.0 mL, 10 mmol) was added to a solution of 3-bromopyridine (1.60 g, 10.0 mmol) in THF (15 mL) under nitrogen atmosphere at room temperature and the mixture was stirred for 1 h. Vinylboronic acid dibutyl ester (3.4 mL) was added to the reaction dropwise 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-91d298af688546b7951e5fc808023a81
Source dataset
uspto-grants-2011_02
Patent number
US07888356B2

Reaction notes

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