Trifluoroacetic acid → 5-(2-Amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one
Reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:25]2[NH:26][CH:27]=[CH:28][CH:29]=2)[C:14]2[C:15](=[O:24])[NH:16][C:17]3[C:22]=2[C:21]=1[C:20]([F:23])=[CH:19][CH:18]=3)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:25]2[NH:26][CH:27]=[CH:28][CH:29]=2)[C:14]2[C:15](=[O:24])[NH:16][C:17]3[C:22]=2[C:21]=1[C:20]([F:23])=[CH:19][CH:18]=3Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of [2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-yloxy]-ethyl]-carbamic acid tert-butyl ester (from Example 18 above) (16.5 mg, 0.2 mmol) in CH2Cl2 (1 mL) was added trifluoroacetic acid (0.5 mL) at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was quenched with 1.0 N NaOH (2.0 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 5-(2-amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 11.2 mg, 89.7%).
Workup
- customthe reaction mixture was quenched with 1.0 N NaOH (2.0 mL)
- extractionextracted with ethyl acetate (3×30 mL)
- washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9901977dfc854b728a960590901a2136
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531598B1
Reaction notes
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