Pyridine → HCID 53754941, compound

HRID 1597919Notes

Reaction equation

HRID 1597919 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]3[O:31][CH2:30][CH2:29][O:28][C:25]=3[CH:26]=2)[N:21]=[CH:20][N:19]=1>CC(O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:18]2[C:27]3[C:22](=[CH:23][C:24]4[O:31][CH2:30][CH2:29][O:28][C:25]=4[CH:26]=3)[N:21]=[CH:20][N:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2585676-Chloro-2,3-dihydro-1h-indoleHCID 189328674-Chloro-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline

Product 1

HCID 53754941HCID 53754941, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 6-chloroindoline (52 mg, 0.339 mmol) and pyridine (23.3 mg, 0.294 mmol) in i-PrOH (3 mL) was added 4-chloro-6,7-(ethylenedioxy)quinazoline (65 mg, 0.284 mmol). The mixture was heated to reflux under dry N2(g) for 16 hours and then concentrated in vacuo. The residue was partitioned between CHCl3 and saturated aqueous NaHCO3, and the organic phase was washed with brine, dried over Na2SO4(s), and concentrated in vacuo. The residue was flash chromatographed on silica using 30% acetone/hexanes to afford 84 mg of 4-(6-chloro-2,3-dihydro-indol-1-yl)-7,8-dihydro-[1,4]dioxino [2,3-g]quinazoline as its free-base (M.P. 209°-211° C.; GC/MS: 339 (M+); anal. RP18-HPLC RT: 5.02 min).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under dry N2(g) for 16 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between CHCl3 and saturated aqueous NaHCO3
  5. washthe organic phase was washed with brine
  6. dry with materialdried over Na2SO4(s)
  7. concentrationconcentrated in vacuo
  8. customchromatographed on silica using 30% acetone/hexanes

Sources & evidence

ORD record
ord-c77206b4a7914c38b338918d8d8cc20c
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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