Water → 3-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamine

HRID 2401622Notes

Reaction equation

HRID 2401622 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:14]=1[CH2:15]Br.O>CO>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:14]=1[CH2:15][O:11][C:10]1[C:5]([NH2:4])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 102634983-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At RT, 51 g of sodium methoxide (953 mmol, 1.05 equivalents) were initially charged in 1000 ml of methanol, 100 g of 2-amino-3-hydroxypyridine (908 mmol, 1 equivalent) were added and the mixture was stirred at RT for another 15 min. The reaction mixture was concentrated under reduced pressure, the residue was taken up in 2500 ml of DMSO and 197 g of 2,6-difluorobenzyl bromide (953 mmol, 1.05 equivalents) were added. After 4 h at RT, the reaction mixture was poured into 20 l of water and stirred for 15 min, the solid was filtered off, washed with 1 l of water, 100 ml of isopropanol and 500 ml of petroleum ether and dried under high vacuum. This gave 171 g of the title compound (78% of theory).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. waitAfter 4 h at RT
  3. stirringstirred for 15 min
  4. filtrationthe solid was filtered off
  5. washwashed with 1 l of water, 100 ml of isopropanol and 500 ml of petroleum ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-26b82b6ade4a4ecf92f6f4f0d00c9f64
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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