Nitrogen → 2-Bromo-4-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

HRID 42775Notes

Reaction equation

HRID 42775 reaction equation
N#N.[Br:3][C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][N:5]=1.COC([O:18][CH3:19])OC.[C:20]([O-])([O-])=O.[Na+].[Na+]>C(O)CO>[Br:3][C:4]1[CH:9]=[C:8]([C:10]2([CH3:11])[O:18][CH2:19][CH2:20][O:12]2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 150910131-(2-Bromopyridin-4-yl)ethan-1-one

Product 1

HCID 866494792-Bromo-4-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-(2-bromo-pyridin-4-yl)-ethanone (1650 mg, 8.25 mmol) in ethylene glycol (8.8 mL) was treated with trimethylorthoformate (1.85 mL, 16.88 mmol) followed by LiBF4 (158 mg, 1.65 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. Na2CO3 (20 mL) was added and the mixture was extracted with Et2O (2×30 mL). The org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (6:1 to 2:1 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:1 hept-EA)=0.57. LC-MS-conditions 02: tR=0.88 min; [M+H]+=244.19.

Workup

  1. extractionthe mixture was extracted with Et2O (2×30 mL)
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (6:1 to 2:1 hept-EA)

Sources & evidence

ORD record
ord-7d2dd118fae043278e451ba757c7b3a8
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

Loading…