Trifluoroacetic acid → 4-Fluoro-5-iodo-2-pyridinamine

HRID 1777868Notes

Reaction equation

HRID 1777868 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C1C(=O)N([I:16])C(=O)C1.C(O)(C(F)(F)F)=O>CC#N.CCOC(C)=O>[F:1][C:2]1[C:7]([I:16])=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 183278082-Amino-4-fluoropyridine

Product 1

HCID 717211424-Fluoro-5-iodo-2-pyridinamine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-fluoropyridin-2-amine (336 g, 2.5 mol) and NIS (745 g, 2.75 mol) in MeCN (9 l) was treated with TFA (114 g, 1 mol). The reaction mixture was then stirred at room temperature for 8 h. The reaction mixture was diluted with EtOAc (10 l), washed with sat. aq. Na2S2O3 (2×5 l), brine (4×5 l). The combined organic layers were dried over Na2SO4, filtered and concentrated to get the crude product. The crude product was purified by recrystallization from EtOAc/pentane (1/10) to afford the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.14 (d, 1H), 6.45 (s, 2H), 6.33 (d, 1H).

Workup

  1. washwashed with sat. aq. Na2S2O3 (2×5 l), brine (4×5 l)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto get the crude product
  6. customThe crude product was purified by recrystallization from EtOAc/pentane (1/10)

Sources & evidence

ORD record
ord-67d35ccfc9bd4bf6a1cce90f69a16cda
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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