Imidazole → HCID 68910871, compound

HRID 1191382Notes

Reaction equation

HRID 1191382 reaction equation
O[CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:41]I>C(Cl)Cl>[I:41][CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68910188HCID 68910188, compound

Product 1

HCID 68910871HCID 68910871, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction flask was charged with (S)-1-(3-Hydroxy-2-methylpropyl)-3,4-dihydro-1H-quinolin-2-one (122LH16) (1.54 g, 7.0 mmol) dissolved in 50 mL DCM. PPh3 (4.04 g, 15.4 mmol) and imidazole (1.14 g, 16.7 mmol) were added followed by stirring at rt for 15 min. The mixture was cooled with an ice-bath followed by addition of I2 (5.00 g, 19.7 mmol). The reaction mixture was slowly warmed to rt and stirred over night. The reaction mixture was washed with a Na2S2O3 solution, dried over Na2SO4, and concentrated. The product was purified by flash CC (SiO2; n-heptane/EtOAc 1:1) to give the title compound (122LH18) (2.140 g, 93%).

Workup

  1. temperatureThe mixture was cooled with an ice-bath
  2. temperatureThe reaction mixture was slowly warmed to rt
  3. stirringstirred over night
  4. washThe reaction mixture was washed with a Na2S2O3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe product was purified by flash CC (SiO2; n-heptane/EtOAc 1:1)

Sources & evidence

ORD record
ord-39b87e32049447ac820b81b53db83bae
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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