Trifluoroacetic acid → HCID 69097147, compound

HRID 2409952Notes

Reaction equation

HRID 2409952 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[C:15]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([Cl:28])=[C:23]([O:29][CH3:30])[CH:22]=2)([CH3:18])([CH3:17])[CH3:16].[CH:31]([C:33]1[N:38]=[C:37]([C:39]([O:41][CH3:42])=[O:40])[CH:36]=[CH:35][CH:34]=1)=O.C(=O)([O-])O.[Na+]>ClCCl.O>[C:15]([C:19]1[NH:20][C:21]2[C:26]([C:27]=1[CH2:31][C:33]1[N:38]=[C:37]([C:39]([O:41][CH3:42])=[O:40])[CH:36]=[CH:35][CH:34]=1)=[CH:25][C:24]([Cl:28])=[C:23]([O:29][CH3:30])[CH:22]=2)([CH3:18])([CH3:16])[CH3:17]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 12575850Methyl 6-formylpyridine-2-carboxylateHCID 69097053HCID 69097053, compound

Product 1

HCID 69097147HCID 69097147, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triethylsilane (0.202 mL) and trifluoroacetic acid (0.049 mL) in dichloromethane (2 mL) was added a suspension of 2-tert-butyl-5-chloro-6-methoxy-1H-indole (100 mg) and methyl 6-formylpyridine-2-carboxylate (76.2 mg) in dichloromethane (1.5 mL) under ice-cooling, and this mixture was stirred at room temperature overnight. To the reaction mixture was added water, and then the resulting mixture was alkalified by the addition of sodium hydrogen carbonate. The organic layer was separated and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (152 mg). 1H-NMR (CDCl3) δ ppm: 1.39 (9H, s), 3.90 (3H, s), 4.05 (3H, s), 4.52 (2H, s), 6.91 (1H, s), 6.95-7.05 (1H, m), 7.28 (1H, s), 7.60 (1H, t, J=7.8 Hz), 7.80-8.20 (2H, m).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6b60012c1c02454bb4487158abc4ad23
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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