4-Methoxybenzylamine → (3-Bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-amine

HRID 1749091Notes

Reaction equation

HRID 1749091 reaction equation
[Br:1][C:2]1[C:3]([CH2:9]Br)=[N:4][C:5]([F:8])=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>ClCCl>[Br:1][C:2]1[C:3]([CH2:9][NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[N:4][C:5]([F:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 726988773-Bromo-2-(bromomethyl)-6-fluoropyridine

Product 1

HCID 70981253(3-Bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-amineYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-bromo-2-bromomethyl-6-fluoro-pyridine (2.70 g, 10.0 mmol, 1.0 equiv) in dichloromethane (20 mL) was added a solution of 4-methoxybenzylamine (2.74 g, 20.0 mmol, 2.0 equiv) in dichloromethane (5 mL) and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was diluted with dichloromethane, washed with H2O, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-50%) to afford (3-bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-amine (1.2 g). MS: [M+H]+=326.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-50%)

Sources & evidence

ORD record
ord-2df944e72ac54fd9be8f7dbcf1f64953
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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