Dichloromethane → 7-[(4-fluorophenyl)methyl]-9-hydroxy-5,6-dimethoxy-6H-pyrrolo[3,4-g]quinolin-8-one

HRID 853629Notes

Reaction equation

HRID 853629 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:22][CH3:23])[C:9]=3[CH:8]2[OH:24])=[CH:4][CH:3]=1.[CH2:27](Cl)Cl.C(O)(C(F)(F)F)=O>CO>[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]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:22][CH3:23])[C:9]=3[CH:8]2[O:24][CH3:27])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 103834717-[(4-fluorophenyl)methyl]-6,9-dihydroxy-5-methoxy-6H-pyrrolo[3,4-g]quinolin-8-one

Product 1

HCID 117265107-[(4-fluorophenyl)methyl]-9-hydroxy-5,6-dimethoxy-6H-pyrrolo[3,4-g]quinolin-8-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 21 (6.7 mg, 0.019 mmol) in a 1:1 solution of CH2Cl2:MeOH was stirred with TFA (3 μL, 0.038 mmol) at room temperature for 2 hours when complete conversion was observed by LCMS. The solution was dried in vacuo and the residue was washed with hexanes to yield 7 mg of the product 22. EI MS (m/z) 355.4 [MH+].

Workup

  1. customThe solution was dried in vacuo
  2. washthe residue was washed with hexanes

Sources & evidence

ORD record
ord-c1d42bc97f7f451f9c0043752017028e
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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