Triphenylphosphine → Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate

HRID 1251930Notes

Reaction equation

HRID 1251930 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:21][N:22]1[C:26]([CH2:27][CH:28]([C:30]2[S:31][CH:32]=[CH:33][N:34]=2)O)=[CH:25][N:24]=[CH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([O:18][CH:28]([C:30]3[S:31][CH:32]=[CH:33][N:34]=3)[CH2:27][C:26]3[N:22]([CH3:21])[CH:23]=[N:24][CH:25]=3)=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 183244102-(1-Methylimidazol-5-yl)-1-(thiazol-2-yl)ethanolHCID 18324453Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate

Product 1

HCID 18324499Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoateYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (1.83 g, 6.7 mmol), 2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethanol (1.40 g, 6.68 mmol) and triphenylphosphine (2.10 g, 8.0 mmol) in tetrahydrofuran (25 ml) was stirred at ambient temperature under a nitrogen atmosphere. DEAD (1.39 g, 1.25 ml 8.0 mmol) was added dropwise to the solution. (The reaction was maintained at ambient temperature ±2° C.). The orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The tetrahydrofiran solution was evaporated to dryness to give an oil. Purification by flash column chromatography eluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1) gave methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate (2.07 g, 67%) as a clear oil.

Workup

  1. temperature(The reaction was maintained at ambient temperature ±2° C.)
  2. stirringThe orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours
  3. customThe tetrahydrofiran solution was evaporated to dryness
  4. customto give an oil
  5. customPurification by flash column chromatography
  6. washeluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1)

Sources & evidence

ORD record
ord-cd43111c01b94a9795f823b34edf47bb
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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