Sodium Iodide → HCID 9836317, compound

HRID 983911Notes

Reaction equation

HRID 983911 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([S:12][CH2:13][CH2:14]3)=[C:10]([CH2:16]O)[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C(#N)C.[I-].[Na+].C[Si](Cl)(C)C>C1COCC1.[Zn].O.C(O)(=O)C.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:15]3[C:11]([S:12][CH2:13][CH2:14]3)=[C:10]([CH3:16])[C:9]=2[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:6][CH:7]=1

Participants

10

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 9901870HCID 9901870, compound

Product 1

HCID 9836317HCID 9836317, compoundYield 71.6%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The compound of example 12 (2.05 g, 6.3 mmol) is brought into solution in a mixture of abs. acetonitrile (16 ml), glacial acetic acid (1.6 ml) and a little abs. DMF at 50° C., sodium iodide (2.35 g, 15.7 mmol) is added and then trimethylsilyl chloride (TMSCl, 1.6 ml, 1.37 g, 12.7 mmol) is added dropwise. The temperature of the batch is kept at 50° C. for 2 h. Glacial acetic acid (1.6 ml) and zinc powder (2.87 g, 44 mmol) is added in three portions and the mixture is stirred at 80° C. for 16 h. The mixture is cooled, treated with a little water and extracted with CH2Cl2. The CH2Cl2 extracts are dried over Na2SO4 sicc. and concentrated. The residue obtained is taken up in THF and eluted through Al2O3 (50 g) using THF. From the residue (1.4 g) obtained after evaporation of the THF, using acetone 0.6 g of pale yellow substance (94%; HPLC: RP 18; acetonitrile/NaH2PO4 buffer 70:30) is obtained, which is recrystallized from MeOH in the presence of heat: 0.43 g of pale yellow powder.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with CH2Cl2
  3. dry with materialThe CH2Cl2 extracts are dried over Na2SO4 sicc
  4. concentrationand concentrated
  5. customThe residue obtained
  6. washeluted through Al2O3 (50 g)

Sources & evidence

ORD record
ord-7d5cd4b1b79b4cb28547b9439ec2c82b
Source dataset
uspto-grants-2005_03
Patent number
US06867211B2

Reaction notes

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