Triphenylphosphine → HCID 22507076, compound

HRID 985485Notes

Reaction equation

HRID 985485 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CN[C:11]1[N:16]=[C:15]([CH2:17][CH2:18]O)[CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:39]([C:46](OCC)=O)=NC(OCC)=O>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:18][CH2:17][C:15]1[N:16]=[C:11]([CH2:46][NH2:39])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 122723-IodophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 105348582-[6-(Methylamino)-2-pyridyl]ethan-1-ol

Product 1

HCID 22507076HCID 22507076, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3-iodophenol (1.11 g, 5.1 mmol), 2-[6-(Methylamino)-2-pyridyl]ethan-1-ol (700 mg, 4.6 mmol), triphenylphosphine (1.3 g, 5.1 mmol), and THF (20 ml), was added diethyl azodicarboxylate (0.80 ml, 5.1 mmol) at 0° C. After stirring overnight under argon at room temperature, the solvent was evaporated under vacuum. The crude product was chromatographed over silica gel to yield 1.2 g (74%) of {6-[2-(3-Iodophenoxy)ethyl](2-pyridyl)}methylamine. NMR 1H Cl3CD δ: 7.40 (t, 1H, J=8.0 Hz), 7.26 (m, 2H), 6.96 (t, 1H, J=8.0 Hz), 6.87 (m, 1H), 6.52 (d, 1H, J=8.0 Hz), 6.25 (d, 1H, J=4.0 Hz), 4.51 (br s, 1H), 4.29 (t, 2H, J=6.8 Hz), 3.07 (t, 2H, J=6.8 Hz), 2.90 (d, 3H, J=8Hz).

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-624985cfde0f4662a160250db1107bba
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

Loading…