Sodium Iodide → 5-Methoxy-9-(4-methoxy-benzyloxy)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

HRID 853701Notes

Reaction equation

HRID 853701 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.[I-].[Na+].[OH:19][C:20]1[C:21]2[C:34](=[O:35])[NH:33][CH2:32][C:22]=2[C:23]([O:30][CH3:31])=[C:24]2[C:29]=1[N:28]=[CH:27][CH:26]=[CH:25]2>FC1C=CC(CN2C(=O)C3C(OCOC)=C4C(C=CC=N4)=C(OC)C=3C2=O)=CC=1.C(O)(=O)C>[CH3:31][O:30][C:23]1[C:22]2[CH2:32][NH:33][C:34](=[O:35])[C:21]=2[C:20]([O:19][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[C:29]2[C:24]=1[CH:25]=[CH:26][CH:27]=[N:28]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 589286969-Hydroxy-5-methoxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Product 1

HCID 589287845-Methoxy-9-(4-methoxy-benzyloxy)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-oneYield 53%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 589288257-(4-Fluoro-benzyl)-5-methoxy-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dioneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (60.1 mg, 0.435 mmol), 4-methoxybenzylchloride (41 mg, 0.26 mmol), and sodium iodide (6.3 mg, 0.043 mmol) were added to 9-hydroxy-5-methoxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 303 (20 mg, 0.087 mmol) dissolved in dimethylformamide 8 (0.4 ml). The reaction mixture was warmed to 60° C. and stirred at 60° C. for one hour. After cooling the reaction mixture to 0° C., acetic acid (0.06 ml) was added and the mixture was concentrated in vacuo. The residue was diluted with ethyl acetate and washed once with 5% Citric Acid, twice with water, once with brine, and concentrated in vacuo. The residue was purified by silica gel chromatography (9/1-dichloromethane/methanol) to afford 5-methoxy-9-(4-methoxy-benzyloxy)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 304 (16 mg, 0.046 mmol, 53%). 1H NMR (CDCl3) δ 9.0 (dd, 1H), 8.64 (dd, 1H), 7.51 (d, 2H), 7.46 (m, 1H), 6.80 (d, 2H), 6.50 (broad, 1H), 5.60 (s, 2H), 3.98 (s, 3H), 3.72 (s, 3H). MS: 351.1 (M+1).

Workup

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. concentrationthe mixture was concentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed once with 5% Citric Acid, twice with water, once with brine
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (9/1-dichloromethane/methanol)

Sources & evidence

ORD record
ord-e0b0b754304c46b6b17740c7e5bbcc0b
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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