Triphenylphosphine → 1-(4-Bromopyridin-2-yl)ethanamine

HRID 879582Notes

Reaction equation

HRID 879582 reaction equation
[N:1]([CH:4]([C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][N:7]=1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Br:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH:4]([NH2:1])[CH3:5])[CH:11]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 867003992-(1-Azidoethyl)-4-bromopyridine

Product 1

HCID 826584741-(4-Bromopyridin-2-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(1-azidoethyl)-4-bromopyridine (4.08 g, 16.54 mmol) in THF (100 mL) and water (10 mL) was added polymer-bound triphenylphosphine (200-400 mesh, -3 mmol/g loading; 10.97 g, 32.94 mmol). The suspension was then stirred at room temperature for 7 hours. The reaction was filtered over a coarse frit twice, then concentrated to afford the crude product which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=5.2 Hz, 1H), 7.52 (s, 1H), 7.32 (dd, J=5.2, 1.6 Hz, 1H), 4.13 (q, J=6.7 Hz, 1H), 1.83 (br s, 2H), 1.41 (d, J=6.7 Hz, 3H).

Workup

  1. filtrationThe reaction was filtered over a coarse frit twice
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-86a148b1f9d840a681efff087d9b705e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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