Trifluoroacetic acid → HCID 57908499, compound

HRID 2426990Notes

Reaction equation

HRID 2426990 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][C:3]1[C:4]2[C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 114773-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 57908499HCID 57908499, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available methyl 1H-indole-4-carboxylate (5 g, 28.5 mmol) in 100 mL dichloromethane, at 0° C., was added 3-chlorobenzaldehyde (5 mL, 43.8 mmol), triethylsilane (15 mL, 93.9 mmol) and trifluoroacetic acid (5 mL, 64.9 mmol), and the resulting solution was stirred for ON as it warmed to rt. The reaction was then quenched with saturated aqueous sodium bicarbonate and the solution was extracted with dichloromethane. The organic phases were then combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resultant solid was washed with cold 10:1 hexanes:dichloromethane to yield 6 g of the title compound as a white solid. 1H NMR (500 MHz, d6-acetone): δ 8.5 (s, 1H), 8.0 (m, 2H), 7.4-7.1 (m, 5H), 5.7 (s, 2H), 4.0 (s, 3H).

Workup

  1. customThe reaction was then quenched with saturated aqueous sodium bicarbonate
  2. extractionthe solution was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe resultant solid was washed with cold 10:1 hexanes

Sources & evidence

ORD record
ord-f39f2c2d7b2341a8b3e101766aa9f0b0
Source dataset
uspto-grants-2011_06
Patent number
US07968578B2

Reaction notes

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