Triphenylphosphine → HCID 24957696, compound

HRID 1097786Notes

Reaction equation

HRID 1097786 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][C:31]1([CH3:49])[CH3:48].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][C:31]2([CH3:49])[CH3:48])[CH:2]=[N:1][CH:5]=1)=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59277701HCID 59277701, compoundHCID 178418785HCID 178418785, compound

Product 1

HCID 24957696HCID 24957696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

methyl 4-imidazolecarboxylate (55 mg, 0.44 mmol), PS-triphenylphosphine (2.15 mmol/g, 0.20 g, 0.43 mmol) are added to a solution of (4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (80 mg, 0.28 mmol) in THF (10 mL) at room temperature. The mixture is stirred at room temperature for 5 minutes and then Cooled to 0° C. DIAD (0.083 mL, 0.43 mmol) is added, and then the mixture is stirred at room temperature. After 3 h, the reaction mixture is filtered to remove resin and washed with ethyl acetate. The ethyl acetate solution is washed with brine, and dried over anhydrous sodium sulfate. After concentration, the residue is purified by reverse phase HPLC (CH3CN:H2O=20 to 90% over 20 mins) and yields the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.74 (s, 3 H), 1.15 (s, 3 H), 3.52 (d, J=13.4 Hz, 1 H), 3.87 (d, J=13.1 Hz, 1 H), 3.92 (s, 3 H), 5.30 (s, 1 H), 6.40 (s, 1 H), 6.95-6.99 (m, 1 H), 7.01-7.06 (m, 1 H), 7.11-7.16 (m, 1 H), 7.28-7.33 (m, 2 H), 7.38-7.44 (m, 2 H), 7.45-7.50 (m, 1 H), 7.52-7.56 (m, 2 H). HRMS: calculated for C23H24N3O3: 390.1818. Found: 390.1800

Workup

  1. temperatureCooled to 0° C
  2. stirringthe mixture is stirred at room temperature
  3. waitAfter 3 h
  4. filtrationthe reaction mixture is filtered
  5. customto remove resin
  6. washwashed with ethyl acetate
  7. washThe ethyl acetate solution is washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationAfter concentration
  10. customthe residue is purified by reverse phase HPLC (CH3CN:H2O=20 to 90% over 20 mins)

Sources & evidence

ORD record
ord-43086f1c91a5499abe15985472158ca7
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

Loading…