Trifluoroacetic acid → HCID 57756251, compound

HRID 594016Notes

Reaction equation

HRID 594016 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:14]([CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)=[C:13]([I:25])[CH:12]=[CH:11][N:10]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:8][C:9]1[C:14]([CH2:15][CH2:16][NH2:17])=[C:13]([I:25])[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 23657231HCID 23657231, compound

Product 1

HCID 57756251HCID 57756251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TFA (0.677 ml, 8.79 mmol) was added into a solution of tert-butyl 2-(2-fluoro-4-iodopyridin-3-yl)ethylcarbamate (1.61 g, 4.40 mmol) in DCM (6.28 ml, 4.40 mmol). After 4 h, LCMS showed mainly starting material. 1 mL of TFA was added. After 16 h, the reaction was diluted with DCM, neutralized with sat. NaHCO3. The product was extracted with DCM. The organic layer was washed with brine, dried over MgSO4, and concentrated to afford a creamy colored solid, 2-(2-fluoro-4-iodopyridin-3-yl)ethanamine MS Calcd for C7H8FIN2: [M]+=266. Found: [M+H]+=267. HRMS Calcd for C7H8FIN2: [M+H]+=266.9789. Found: [M+H]+=266.9802.

Workup

  1. waitAfter 16 h
  2. extractionThe product was extracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c398499cde6043378fccd8a59098f004
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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