Triethylamine → HCID 86707946, compound

HRID 2400294Notes

Reaction equation

HRID 2400294 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:8]2[CH2:11][C:12]2[O:16][C:15]([C:17]([NH2:19])=O)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:26][CH3:27].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:8]2[CH2:11][C:12]2[O:16][C:15]([C:17]#[N:19])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 86707945HCID 86707945, compound

Product 1

HCID 86707946HCID 86707946, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(6-chloro-5-methoxy-2-phenylindol-1-ylmethyl)furan-2-carboxamide (194 mg) in dichloromethane (2.5 mL) were successively added triethylamine (0.355 mL) and trifluoroacetic anhydride (0.177 mL) under ice-cooling. This mixture was stirred at room temperature for 8 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (143 mg). 1H-NMR (CDCl3) δ ppm: 3.95 (3H, s), 5.23 (2H, s), 6.00-6.10 (1H, m), 6.50-6.60 (1H, m), 6.98 (1H, d, J=3.6 Hz), 7.16 (1H, s), 7.25-7.35 (1H, m), 7.40-7.55 (5H, m).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-61e2de234ac04c37ab679119a651345f
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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