Pyridine → HCID 9798097, compound

HRID 1597921Notes

Reaction equation

HRID 1597921 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][NH:9]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1>CC(O)C>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 189328756-Chloro-2,3-dihydro-1H-indole--hydrogen chloride (1/1)

Product 1

HCID 9798097HCID 9798097, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 6-chloroindoline hydrochloride (1 00 mg, 0.526 mmol) and pyridine (0.957 mmol, 77 μL) in dry i-PrOH (8 mL) was added 4-chloro-6,7-dimethoxyquinazoline (107 mg, 0.478 mmol). The mixture was refluxed for 2 hours under an atmosphere of dry N2(g) and then the solvent was removed in vacuo. The residue was partitioned between CHCl3 and 1M NaOH, and the organic phase was washed with brine, dried over Na2SO4(g) and concentrated in vacuo. The residue (171 mg) was purified by flash chromatography on silica using 80%EtOAc/CH2 Cl2 to yield 4-(6-chloro-2,3-dihydro-indol-1-yl)-6,7-dimethoxy-quinazoline as its free base (148 mg) (M.P. 229°-230° C.; LC-MS: 342 (MH+); anal. RP18-HPLC RT: 4.38 min.).

Workup

  1. temperatureThe mixture was refluxed for 2 hours under an atmosphere of dry N2(g)
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between CHCl3 and 1M NaOH
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4(g)
  6. concentrationconcentrated in vacuo
  7. customThe residue (171 mg) was purified by flash chromatography on silica using 80%EtOAc/CH2 Cl2

Sources & evidence

ORD record
ord-f3ebcff4d1714bed8453c727bcd8bc72
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…