Water → (R)-1-((3-amino-6-bromopyridin-2-yl)(benzyl)amino)propan-2-ol

HRID 1485682Notes

Reaction equation

HRID 1485682 reaction equation
[Cl-].[NH4+].O.[CH2:4]([N:11]([C:16]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[C:18]([Br:25])[N:17]=1)[CH2:12][C@H:13]([OH:15])[CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.[Fe]>[NH2:22][C:21]1[C:16]([N:11]([CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:12][C@H:13]([OH:15])[CH3:14])=[N:17][C:18]([Br:25])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 118079393(R)-1-(benzyl(6-bromo-3-nitropyridin-2-yl)amino)propan-2-ol

Product 1

HCID 118078844(R)-1-((3-amino-6-bromopyridin-2-yl)(benzyl)amino)propan-2-olYield 80.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

A 100-mL round bottomed flask equipped with a magnetic stir bar was charged with ammonium chloride (0.044 g, 0.820 mmol), water (8.2 mL), iron powder (4.58 g, 82 mmol), and ethanol (21.8 mL). The mixture was heated to 80° C., and a solution of (R)-1-(benzyl(6-bromo-3-nitropyridin-2-yl)amino)propan-2-ol (3.00 g, 8.2 mmol) in ethanol (8.20 mL) was slowly added over 2 min. The reaction mixture was stirred at 80° C. After 90 min, heating was discontinued and the reaction mixture filtered through a pad of Celite. The flask and Celite pad were rinsed with ethanol. The filtrate was concentrated. The residue was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (20 mL). The ethyl acetate layer was washed with 5% aqueous sodium chloride solution (20 mL) and concentrated under reduced pressure to afford crude (R)-1-((3-amino-6-bromopyridin-2-yl)(benzyl)amino)propan-2-ol (2.22 g) as a dark syrup. MS (ESI, pos. ion) m/z 336, 338 [M+1]+.

Workup

  1. customA 100-mL round bottomed flask equipped with a magnetic stir bar
  2. temperatureheating
  3. filtrationthe reaction mixture filtered through a pad of Celite
  4. washThe flask and Celite pad were rinsed with ethanol
  5. concentrationThe filtrate was concentrated
  6. customThe residue was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (20 mL)
  7. washThe ethyl acetate layer was washed with 5% aqueous sodium chloride solution (20 mL)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d277322e177f4262816d263d5ba0da9b
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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