Trifluoroacetic acid → Trifluoroacetic acid

HRID 853687Notes

Reaction equation

HRID 853687 reaction equation
C([O:14][C:15]1[C:16]2[C:27](=[O:28])[N:26]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH2:25][C:17]=2[CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C1C=CC=CC=1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].C([SiH](CC)CC)C>ClCCl>[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[C:27](=[O:28])[C:16]3[C:15]([OH:14])=[C:24]4[C:19]([CH:20]=[CH:21][CH:22]=[N:23]4)=[CH:18][C:17]=3[CH2:25]2)=[CH:35][CH:34]=1.[C:39]([OH:41])([C:38]([F:43])([F:42])[F:37])=[O:40]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928791HCID 58928791, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 16072870HCID 16072870, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 283b (11 mg) 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 7-(4-fluoro-benzyl)-9-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 285, TFA salt, (3.9 mg) as a yellow solid: 1H NMR (CDCl3) δ 9.1 (d, 1H), 8.3 (d, 1H), 7.6 (m, 1H), 7.35 (s, 1H), 7.33 (m, 2H), 7.0 (t, 2H), 4.8 (s, 2H), 4.4(s, 2H); MS: 309 (M+1).

Workup

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

Sources & evidence

ORD record
ord-8368637d85414e57ad2c7b96aae071d7
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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