Potassium Carbonate → 7-(4-Fluoro-benzyl)-5-hydroxy-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853616Notes

Reaction equation

HRID 853616 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][CH2:22][O:23][CH3:24])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:25]C(=O)OCC)[C:9]=3[C:8]2=[O:31])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][CH2:22][O:23][CH3:24])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([OH:25])[C:9]=3[C:8]2=[O:31])=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 58928849Carbonic Acid Ethyl Ester 7-(4-fluoro-benzyl)-9-methoxymethoxy-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl Ester

Product 1

HCID 1361585857-(4-Fluoro-benzyl)-5-hydroxy-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dioneYield 57%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the ethyl carbonate methoxymethyl ether 5 (70.9 mg, 0.156 mmol) in THF (7.6 mL) at room temperature was added a solution (5 mL) of K2CO3 (215 mg, 1.56 mmol) in water and 4-dimethylaminopyridine (3.8 mg, 0.03 mmol). The yellow solution was stirred at room temperature under nitrogen atmosphere overnight. Most of THF was removed under reduced pressure at 30-40° C. and the remaining solution was diluted with dichloromethane, washed with 1N HCl and brine, dried (MgSO4) and concentrated to give solid crude product (51 mg, 85%), which is triturated in diethylether/hexane to afford the product, 7-(4-fluoro-benzyl)-5-hydroxy-9-methoxymethoxy-pyrrolo [3,4-g]quinoline-6,8-dione 6 as a yellow solid (34 mg). 1H NMR (CDCl3) δ 9.1 (dd, 1H), 8.7 (dd, 1H), 7.6 (dd, 1H), 7.4 (dd, 2H), 7.0 (t, 2H), 5.8 (s, 2H), 4.8 (s, 2H), 3.7 (s, 1H). MS: 383 (M+1); 381 (M-1).

Workup

  1. customMost of THF was removed under reduced pressure at 30-40° C.
  2. additionthe remaining solution was diluted with dichloromethane
  3. washwashed with 1N HCl and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give solid crude product (51 mg, 85%), which
  7. customis triturated in diethylether/hexane

Sources & evidence

ORD record
ord-aab009cc65c045b7af7103da04c13c86
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…