Trifluoroacetic acid → HCID 86695912, compound

HRID 870918Notes

Reaction equation

HRID 870918 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14]C(=O)OC(C)(C)C)[C:9]=2[CH:22]=[O:23])=[C:4]([F:24])[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:14][C:10]1[N:11]=[CH:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:24])[C:9]=1[CH:22]=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695909HCID 86695909, compound

Product 1

HCID 86695912HCID 86695912, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (4-(4-chloro-2-fluorophenyl)-3-formylpyridin-2-yl)carbamate (0.9 g, 2.57 mmol) in CH2Cl2 (15 mL) was added TFA (3.95 mL, 51.3 mmol) and the reaction mixture was stirred at room temperature for 3 h. The reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (15 mL) and extracted with CH2Cl2 (2×15 mL). The combined organic extracts were washed with brine (1×15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude 2-amino-4-(4-chloro-2-fluorophenyl)nicotinaldehyde (0.6 g, 2.40 mmol, 41% yield) was carried into the next step without further purification. LCMS (ESI) m/e 251.0 [(M+H)+, calcd for C12H9ClFN2O 251.0]; LC/MS retention time (Method C): tR=1.67 min.

Workup

  1. customThe reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (15 mL)
  2. extractionextracted with CH2Cl2 (2×15 mL)
  3. washThe combined organic extracts were washed with brine (1×15 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cc9dc448bcd465c84bd8c2b14dea236
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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