Diazomethane → 3-bromo-4-cyclopropylpyridine

HRID 1521567Notes

Reaction equation

HRID 1521567 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[CH2:9].[N+](=[CH2:12])=[N-]>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:12][CH2:9]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 667936541255957-49-3

Product 1

HCID 667140493-bromo-4-cyclopropylpyridine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-bromo-4-vinylpyridine (Z, 0.4 g, 2.2 mmol) in ether (20 mL) was added palladium acetate (catalytic) and diazomethane (required for preparation, N-nitroso-N-methylurea-1.03 g, 10.0 mmol; 40% potassium hydroxide, 10 mL; ether, 20 mL) portion wise at 0° C. for 10 min. The reaction mixture was stirred at 0° C. for 0.5 h. The reaction mixture was filter through CELITE bed and concentrated under vacuum to afford the crude compound to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ: 8.62 (s, 1H), 8.34-8.33 (d, J=5.2 Hz, 1H), 6.72-6.71 (d, J=4.8 Hz, 1H), 2.25-2.18 (m, 1H), 1.17-1.12 (m, 2H), 0.80-0.76 (m, 2H). MS (M+2): 200.2.

Workup

  1. filtrationThe reaction mixture was filter through CELITE bed
  2. concentrationconcentrated under vacuum
  3. customto afford the crude compound

Sources & evidence

ORD record
ord-bc842f2583d64866aad6efabb0c8bc09
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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