Trifluoroacetic acid → HCID 86703299, compound

HRID 2409983Notes

Reaction equation

HRID 2409983 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[C:33][C:34]([O:36][CH3:37])=[O:35])[N:27]=3)=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]2C(OC(C)(C)C)=O)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:25][C:26]3[N:27]=[C:28]([C:32]#[C:33][C:34]([O:36][CH3:37])=[O:35])[CH:29]=[CH:30][CH:31]=3)=[C:8]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703300HCID 86703300, compound

Product 1

HCID 86703299HCID 86703299, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 6-methoxy-3-(6-methoxycarbonylethynylpyridin-2-ylmethyl)-2-phenylindole-1-carboxylate (100 mg) in dichloromethane (1 mL) was added trifluoroacetic acid (0.3 mL), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture were added dichloromethane and an aqueous sodium hydrogen carbonate solution, and the organic layer was separated and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (75.1 mg). 1H-NMR (CDCl3) δ ppm: 3.84-3.89 (6H, m), 4.45 (2H, s), 6.75 (1H, dd, J=2.3, 8.8 Hz), 6.92 (1H, d, J=2.3 Hz), 7.04-7.10 (1H, m), 7.31-7.55 (7H, m), 8.09 (1H, br s). ESI-MS (m/z): 397 (M+H)+

Workup

  1. customan aqueous sodium hydrogen carbonate solution, and the organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-49f1d17b8dfa46a5bb7fa5e86e37e1fb
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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