Triphenylphosphine → 3-(1-Benzoyl-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester

HRID 1097784Notes

Reaction equation

HRID 1097784 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]([C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:41])[CH2:32][CH2:31]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:9][O:8][C:6]([C:4]1[N:3]([CH:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([C:40](=[O:41])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:32][CH2:31]2)[CH:2]=[N:1][CH:5]=1)=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59277722N-benzoyl-1,2,3,4-tetrahydroquinolin-4-olHCID 178418785HCID 178418785, compound

Product 1

HCID 592777153-(1-Benzoyl-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

methyl 4-imidazolecarboxylate (200 mg, 1.59 mmol) and PS-triphenylphosphine (2.15 mmol/g, 0.90 g, 1.94 mmol) are added to a solution of (4-hydroxy-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (380 mg, 1.50 mmol) in THF (20 mL) at room temperature. The resulting mixture is stirred at room temperature for 5 minutes and then cooled to 0° C. DIAD (0.38 mL, 1.96 mmol) is added, and the mixture is slowly warmed up to room temperature. After 3 h, the reaction mixture is filtered to remove resin and washed with ethyl acetate. The combined ethyl acetate solution is washed with brine, and dried with anhydrous sodium sulfate. After concentration, the residue is purified by reverse phase HPLC (CH3CN:H2O=10 to 80% over 20 mins) to give the title compound: 1H NMR (400 MHz, CDCl3) δ ppm 2.21-2.30 (m, 1 H), 2.52-2.62 (m, 1 H), 3.75-3.82 (m, 1 H), 3.89 (s, 3 H), 4.11-4.18 (m, 1 H), 6.40 (t, J=6.1 Hz, 1 H), 6.94 (d, J=7.6 Hz, 1 H), 7.01-7.09 (m, 3 H), 7.33-7.40 (m, 3 H), 7.40-7.45 (m, 1 H), 7.46-7.50 (m, 2 H), 7.85 (d, J=0.8 Hz, 1 H).

Workup

  1. temperaturecooled to 0° C
  2. temperaturethe mixture is slowly warmed up to room temperature
  3. waitAfter 3 h
  4. filtrationthe reaction mixture is filtered
  5. customto remove resin
  6. washwashed with ethyl acetate
  7. washThe combined ethyl acetate solution is washed with brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationAfter concentration
  10. customthe residue is purified by reverse phase HPLC (CH3CN:H2O=10 to 80% over 20 mins)

Sources & evidence

ORD record
ord-1df04698d67147ad92a6fefc24c60844
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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