Trifluoroacetic acid → HCID 86695912, compound

HRID 2369509Notes

Reaction equation

HRID 2369509 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]([CH:14]=[O:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[F:23])[CH:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[N:9]=[CH:10][CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[F:23])[C:13]=1[CH:14]=[O:15]

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-295705f939d74d448e73168895a59814
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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