Trifluoroacetic acid → Trifluoroacetic acid

HRID 853679Notes

Reaction equation

HRID 853679 reaction equation
C([O:14][C:15]1[C:16]2[C:36](=[O:37])[N:35]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH2:34][C:17]=2[C:18]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[CH:27][CH:26]=2)=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C1C=CC=CC=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].C([SiH](CC)CC)C>ClCCl>[CH2:32]([O:31][C:28]1[CH:27]=[CH:26][C:25]([C:18]2[C:17]3[CH2:34][N:35]([CH2:38][C:39]4[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=4)[C:36](=[O:37])[C:16]=3[C:15]([OH:14])=[C:24]3[C:19]=2[CH:20]=[CH:21][CH:22]=[N:23]3)=[CH:30][CH:29]=1)[CH3:33].[C:48]([OH:50])([C:47]([F:52])([F:51])[F:46])=[O:49]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928976HCID 58928976, compound

Product 2

HCID 6422Trifluoroacetic acidYield 25%HCID 10071236HCID 10071236, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-benzhydryloxy-5-(4-ethoxy-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 275 (8 mg, 0.013 mmol) dissolved in dichloromethane (1 mL) was added trifluoroacetic acid (100 μl) and triethylsilane (200 μl). The reaction mixture was stirred at room temperature for ½ hours under an inert atmosphere then concentrated in vacuo. The residue was triturated with diethyl ether/hexane (1/1) to afford 5-(4-ethoxy-phenyl)-7-(4-fluoro-benzyl)-9-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 276, TFA salt, (1.8 mg, 0.003 mmol, 25%) as a yellow solid: 1H NMR (CDCl3) δ 9.0 (d, 1H), 8.1 (d, 1H), 7.7 (m, 2H), 7.6 (dd, 1H), 7.5 (dd, 2H), 7.2 (dd, 2H), 7.1 (t, 2H), 4.7 (s, 2H), 4.2(s, 2H), 4.1 (m, 2H), 1.5 (t, 3H); MS: 429 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated with diethyl ether/hexane (1/1)

Sources & evidence

ORD record
ord-5b07f8f90da744c59b8831bc7cf662c8
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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