Triphenylphosphine → HCID 21876153, compound

HRID 1454598Notes

Reaction equation

HRID 1454598 reaction equation
[CH2:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20]O)=[CH:15][CH:14]=2)[C:6]2=[N:7][C:8]([CH3:11])=[CH:9][CH:10]=[C:5]2[N:4]=1)[CH3:2].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:67]=[N+:68]=[N-:69])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH2:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:67]=[N+:68]=[N-:69])=[CH:15][CH:14]=2)[C:6]2=[N:7][C:8]([CH3:11])=[CH:9][CH:10]=[C:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21875895HCID 21875895, compound

Product 1

HCID 21876153HCID 21876153, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[4-(2-ethyl-5-methyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethanol (step 4, 217 mg, 0.77 mmol) in THF (20 mL) was added diethyl azodicarboxylate (DEAD) (0.3 mL, 1.5 mmol), triphenylphosphine (380 mg, 1.5 mmol) and diphenylphosphoryl azide (DPPA) (0.4 mL, 1.5 mmol). The mixture was stirred at room temperature for 4.5 h. After removal of solvent, the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gladient elution from 1:1 to 1:2) to afford 70 mg (30%) of the title compound as a brown oil: 1H-NMR (CDCl3) δ 7.90 (1H, d, J=8.1 Hz), 7.34-7.44 (4H, m), 7.08 (1H, d, J=8.1 Hz), 3.60 (2H, t, J=7.1 Hz), 3.00 (2H, t, J=7.1 Hz), 2.80 (2H, q, J=7.5 Hz), 2.57 (3H, s), 1.35 (3H, t, J=7.5 Hz).

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gladient elution from 1:1 to 1:2)

Sources & evidence

ORD record
ord-15def50712ef451ba784579086225704
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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