Trifluoroacetic acid → Trifluoroacetic acid

HRID 853685Notes

Reaction equation

HRID 853685 reaction equation
[CH2:1]([O:3][C:4](=[O:47])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]2[CH2:21][N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:23](=[O:24])[C:19]=2[C:18]([O:33]C(C2C=CC=CC=2)C2C=CC=CC=2)=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2)[CH3:2].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].C([SiH](CC)CC)C>ClCCl>[CH2:1]([O:3][C:4](=[O:47])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]2[CH2:21][N:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[C:23](=[O:24])[C:19]=2[C:18]([OH:33])=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2)[CH3:2].[C:50]([OH:52])([C:49]([F:54])([F:53])[F:48])=[O:51]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928745HCID 58928745, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44414031HCID 44414031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 281 dissolved in dichloromethane (2 mL) was added trifluoroacetic acid (200 μl) and triethylsilane (400 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 2-[7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl]-benzoic acid ethyl ester 282, TFA salt, (2.5 mg) as a yellow solid: 1H NMR (CD3OD) δ 8.9 (d, 1H), 8.0 (d, 1H), 8.0 (s, 1H), 7.8-7.6 (m, 3H), 7.5 (dd, 1H), 7.3 (m, 2H+1H), 7.0 (t, 2H), 4.7 (dd, 2H), 4.1 (dd, 2H), 3.7 (m, 2H), 0.6 (t, 3H); MS: 457 (M+1).

Workup

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

Sources & evidence

ORD record
ord-c5d62a8d2dae44d7aa6f6e3f10b92667
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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