Trifluoroacetic acid → 9-Hydroxy-5-methoxy-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

HRID 853703Notes

Reaction equation

HRID 853703 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[CH2:13][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:15](=[O:16])[C:11]=2[C:10]([O:28]CC2C=CC(OC)=CC=2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[OH:28][C:10]1[C:11]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH2:13][C:12]=2[C:3]([O:2][CH3:1])=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 589289465-Methoxy-9-(4-methoxy-benzyloxy)-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

Product 1

HCID 104079419-Hydroxy-5-methoxy-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-oneYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-methoxy-9-(4-methoxy-benzyloxy)-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 305 (13 mg, 0.026 mmol) dissolved in dichloromethane (0.200 ml) was added triethylsilane (TES, 0.05 ml) and trifluoroacetic acid (TFA, 0.100 ml). After stirring at room temperature for 15 minutes, the reaction mixture was concentrated in vacuo and azeotroped three times with a (1:1) tetrahydrofuran to toluene mixture. The resulting residue was then triturated three times with a (3:1) hexane to ether mixture to afford 9-hydroxy-5-methoxy-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 306 (7 mg, 0.014 mmol, 54%). 1H NMR (CD3OD) δ 9.0 (dd, 1H), 8.58 (dd, 1H), 7.60 (d, 2H), 7.40 (d, 2H), 4.80 (s, 2H), 4.50 (s, 2H), 3.95 (s, 3H). 19F NMR δ −63, −76.2. MS: 389.1 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customazeotroped three times with a (1:1) tetrahydrofuran to toluene mixture
  3. customThe resulting residue was then triturated three times with a (3:1) hexane to ether mixture

Sources & evidence

ORD record
ord-0c2b3997264342f286b1e0b1db55b6f6
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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