Iodine → HCID 87091918, compound

HRID 1505461Notes

Reaction equation

HRID 1505461 reaction equation
N[C:2]1[C:3]2[C:27]3([CH2:31][CH2:30][O:29][CH2:28]3)[C:26](=[O:32])[NH:25][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:7]=1.[I-:33].[Cs+].II.N(OCCC(C)C)=O>COCCOC.[Cu]I>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:6]2[N:7]=[C:2]([I:33])[C:3]3[C:27]4([CH2:31][CH2:30][O:29][CH2:28]4)[C:26](=[O:32])[NH:25][C:4]=3[N:5]=2)=[N:9]1

Participants

7

Reactant 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 56598426HCID 56598426, compound

Product 1

HCID 87091918HCID 87091918, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

563 mg (1.305 mmol) of the compound obtained in Example 15A were initially charged in 1,2-dimethoxyethane (7.5 ml), and 339 mg (1.305 mmol) of caesium iodide, 165 mg (0.652 mmol) of iodine and 74 mg (0.391 mmol) of copper(I) iodide were then added. Isopentyl nitrite (1.04 ml) was then added, and the mixture was heated at 60° C. for 2 days. After cooling, the mixture was filtered, the filter cake was washed with ethyl acetate and the filtrate was washed twice with 5% strength aqueous sodium thiosulphate solution and once with saturated aqueous sodium chloride solution. The organic phase was then dried over sodium sulphate, filtered and concentrated to dryness. The residue was purified by preparative HPLC (acetonitrile/water (+0.05% formic acid) gradient). This gave 98 mg of the title compound (14% of theory).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washthe filter cake was washed with ethyl acetate
  4. washthe filtrate was washed twice with 5% strength aqueous sodium thiosulphate solution and once with saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was then dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by preparative HPLC (acetonitrile/water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-0284eb83fda243a1bfcd99976ef6621f
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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