2-Fluoro-4-iodoaniline → HCID 24821963, compound

HRID 500512Notes

Reaction equation

HRID 500512 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].F[C:11]1[C:12]([C:18]#[N:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[F:17][C:15]1[CH:16]=[C:11]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:2]=2[F:1])[C:12]([C:18]#[N:19])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium HexamethyldisilazideHCID 27832532-Cyano-3,5-difluoropyridine

Product 1

HCID 24821963HCID 24821963, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution of 2-fluoro-4-iodoaniline (930.5 mg, 3.93 mmol) and 3,5-difluoropyridine-2-carbonitrile (500 mg, 3.57 mmol) in THF (8 mL) at −78° C., was added LiHMDS (6.1 ml, 7.50 mmol). The mixture was allowed to warm to room temperature and stirred for 12 h. The mixture as diluted with ethyl acetate and washed with H2O and brine. The organic layer was dried with solid Na2SO4 and was concentrated. The resulting residue was purified by flash chromatography in silica (25% ethyl acetate-hexane) to give pure product. LC/MS [7.72 min; 358 (M+1)].

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic layer was dried with solid Na2SO4
  3. concentrationwas concentrated
  4. customThe resulting residue was purified by flash chromatography in silica (25% ethyl acetate-hexane)
  5. customto give pure product
  6. customLC/MS [7.72 min; 358 (M+1)]

Sources & evidence

ORD record
ord-145b2da586e84b2ea38704b5bd36f854
Source dataset
uspto-grants-2010_08
Patent number
US07772233B2

Reaction notes

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