Dichloromethane → 3-(Aminomethyl)-5-bromopyridine

HRID 601105Notes

Reaction equation

HRID 601105 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[CH:5]=[N:6][CH:7]=1.FC(F)(F)C(O)=O.ClCCl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22265925Di-tert-butyl(5-bromo-3-pyridinyl)methylimidodicarbonate

Product 1

HCID 229922643-(Aminomethyl)-5-bromopyridineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 18A (0.98 g, 2.53 mmol) was treated with trifluoroacetic acid and dichloromethane (1:1 v/v, 20 mL) for 2 hours at room temperature. The solvent was removed by rotary evaporation and the resulting oil was chased with benzene/dichloromethane (3 times) to give a waxy solid. The salt was dissolved in anhydrous methanol (20 mL) and stirred with Amberlite IRA-400(OH), resin (10 g) for 2 hrs. The resin was removed by vacuum filtration and thoroughly washed with dry methanol. The filtrate was concentrated by rotary evaporation to give the title compound (0.415 g, 88%). MS (DCI/NH3) M/z 187/189 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 3.73 (s, 2H), 8.02 (t, J=2.02 Hz, 1H), 8.50 (d, J=1.47 Hz, 1H), 8.53 (d, J=2.21 Hz, 1H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customto give a waxy solid
  3. customThe resin was removed by vacuum filtration
  4. washthoroughly washed with dry methanol
  5. concentrationThe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-044aa237c36c474a93131174cbfd7fb0
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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