Phosphorus oxybromide → 4-Bromo-2-(1-methylcyclopropyl)pyridine

HRID 2066783Notes

Reaction equation

HRID 2066783 reaction equation
[CH3:1][C:2]1([C:5]2[NH:6][CH:7]=[CH:8][C:9](=O)[CH:10]=2)[CH2:4][CH2:3]1.P(Br)(Br)([Br:14])=O.C([O-])(O)=O.[Na+]>>[Br:14][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)[CH:10]=1

Participants

4

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 552861162-(1-Methylcyclopropyl)pyridin-4(1H)-one

Product 1

HCID 574170884-Bromo-2-(1-methylcyclopropyl)pyridine

Conditions

Temperature
85 °C

Procedure

A mixture of 2-(1-methyl-cyclopropyl)-1H-pyridin-4-one (Step 1.5) (13.4 mmol) and POBr3 (14.74 mmol) was stirred for 15 min at 85° C. and then 15 min at 120° C. After cooling slightly, the reaction mixture was poured into a saturated solution of NaHCO3 and extracted with CH2Cl2 (2×). The combined organic phases were washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a brown oil. HPLC: tR=4.11 min (method B); LC-MS: tR=2.39 min, [M+H]+ 212/214; TLC: Rf=0.31 (CH2Cl2).

Workup

  1. custom15 min
  2. customat 120° C
  3. temperatureAfter cooling slightly
  4. extractionextracted with CH2Cl2 (2×)
  5. washThe combined organic phases were washed with a saturated solution of NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ba5749b75afd4a09821045af077229b0
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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