Bromine → 3-(Benzyloxy)-5-bromopyridin-2-amine

HRID 1624103Notes

Reaction equation

HRID 1624103 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:16]Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:9]([O:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([Br:16])[CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 903342-Amino-3-benzyloxypyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

200 g (1 mol) of 2-amino-3-benzyloxypyridine were initially charged in 4 l of dichloromethane, and a solution of 62 ml (1.2 mol) of bromine in 620 ml of dichloromethane was added at 0° C. over a period of 30 min. After the addition had ended, the reaction solution was stirred at 0° C. for 60 min. About 4 l of saturated aqueous sodium bicarbonate solution were then added to the mixture. The organic phase was separated off and concentrated. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate 6:4), and the product fractions were concentrated. This gave 214 g (77% of theory) of the title compound.

Workup

  1. additionAfter the addition
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate 6:4)
  5. concentrationthe product fractions were concentrated

Sources & evidence

ORD record
ord-aad0379c14484bbaae8b1cab4da3580b
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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