Trifluoroacetic acid → HCID 86703327, compound

HRID 2410012Notes

Reaction equation

HRID 2410012 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]3([CH3:15])[CH2:14][CH2:13]3)[NH:9]2)=[CH:5][C:4]=1[CH3:16].[CH:17]([C:19]1[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=1)=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:17][C:19]3[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3([CH3:15])[CH2:13][CH2:14]3)[NH:9]2)=[CH:5][C:4]=1[CH3:16]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12575850Methyl 6-formylpyridine-2-carboxylateHCID 86703326HCID 86703326, compound

Product 1

HCID 86703327HCID 86703327, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-methoxy-5-methyl-2-(1-methylcyclopropyl)-1H-indole (586 mg) and methyl 6-formylpyridine-2-carboxylate (450 mg) in dichloromethane (13.6 mL) was added triethylsilane (1.30 mL) under ice-cooling. Trifluoroacetic acid (0.313 mL) was added dropwise thereto, and the mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was suspended in methanol. The precipitate was collected by filtration, washed with methanol, and then dried under reduced pressure at 40° C. to obtain the title compound (688 mg). 1H-NMR (CDCl3) δ ppm: 0.66-0.72 (2H, m), 0.80-0.86 (2H, m), 1.31 (3H, s), 2.19 (3H, s), 3.84 (3H, s), 4.05 (3H, s), 4.48 (2H, s), 6.78 (1H, s), 7.00 (1H, s), 7.04-7.10 (1H, m), 7.59 (1H, t, J=7.8 Hz), 7.79 (1H, br s), 7.91-7.97 (1H, m). ESI-MS (m/z): 365 (M+H)+

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with methanol
  9. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-5a170f2ead594c0d9de1558374f64f5b
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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