Pyridine → 2-(2-Hydroxy-3-isopropoxypropyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

HRID 2358306Notes

Reaction equation

HRID 2358306 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]([C:14]#[N:15])=[C:6]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1.[CH:28]([O:31][CH2:32][CH:33]1[O:35][CH2:34]1)([CH3:30])[CH3:29]>CC(O)C>[OH:35][CH:33]([CH2:32][O:31][CH:28]([CH3:30])[CH3:29])[CH2:34][N:8]1[C:7]([C:14]#[N:15])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 199202-((1-Methylethoxy)methyl)oxiraneHCID 112428516-Methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

Product 1

HCID 593892372-(2-Hydroxy-3-isopropoxypropyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 97 (52 mg, 0.19 mmol) in iPrOH (3 mL) were added pyridine (0.03 mL, 0.38 mmol) and glycidyl isopropyl ether (0.047 mL, 0.38 mmol). The resulting mixture was heated to reflux overnight then cooled to room temperature. It was partitioned between EtOAc and NaHCO3. The organic phase was washed with brine, dried (Na2SO4) and concentrated. The product 98 was purified by automated flash chromatography (20-50% EA/Hex).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customIt was partitioned between EtOAc and NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product 98 was purified by automated flash chromatography (20-50% EA/Hex)

Sources & evidence

ORD record
ord-b95c534c5d2c4e609b60575e2c7b3cd3
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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