5-broMo-2-isopropylpyridine → HCID 68558358, compound

HRID 1481367Notes

Reaction equation

HRID 1481367 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[CH2:11](C([Sn])=C(CCCC)CCCC)[CH2:12]CC>CN(C=O)C.C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([CH:11]=[CH2:12])=[CH:7][N:6]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 206055745-broMo-2-isopropylpyridineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 68558358HCID 68558358, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared by following general procedure 2. 5-Bromo-2-isopropyl-pyridine (0.75 g, 3.7 mmol) was dissolved in DMF:THF (3:1, 6 mL). Tributylvinyltin (1.2 mL, 4.12 mmol) and Pd(PPh3)4 (0.070 g, 0.06 mmol) was added to this solution at RT under nitrogen and was heated at 100° C. for 30 min. The reaction mixture was cooled to RT and diluted with water (60 mL) and extracted with DCM (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure below 40° C. The crude was purified through column chromatography (90% DCM-Hexane in silica 100-200 mesh, Diameter of column—5.0 cm, Height of silica—approx. 5 inch) to provide 2-isopropyl-5-vinylpyridine as a light yellow liquid (0.5 g, 90% yield).

Workup

  1. customThe title compound was prepared
  2. temperatureThe reaction mixture was cooled to RT
  3. extractionextracted with DCM (3×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure below 40° C
  6. customThe crude was purified through column chromatography (90% DCM-Hexane in silica 100-200 mesh, Diameter of column—5.0 cm, Height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-54482e37936c45c8addb212b88d8cd8b
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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