Sodium Iodide → HCID 67434669, compound

HRID 1946495Notes

Reaction equation

HRID 1946495 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[C:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(O)[CH2:22][CH2:23][C:19]=3[N:18]=[C:17]2[CH:31]([CH3:33])[CH3:32])=[CH:11][CH:10]=1>C(#N)C>[CH2:29]([O:28][C:26](=[O:27])[CH:25]=[C:21]1[C:20]2[N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=3)[C:17]([CH:31]([CH3:33])[CH3:32])=[N:18][C:19]=2[CH2:23][CH2:22]1)[CH3:30]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 58460230HCID 58460230, compound

Product 1

HCID 67434669HCID 67434669, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of TMSCl (0.252 mL) and sodium iodide (296 mg) in Acetonitrile (3 ml) was added to a stirred suspension of Intermediate 26 (186 mg) in acetonitrile (3 ml). The RM was stirred at room temp under nitrogen overnight. The reaction mixture was partitioned between EtOAc (20 ml) and sat. NaHCO3 aq sol: water (1:1, 20 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (20 ml). The phases were separated, the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (170 mg). LC/MS MH+ 359, 369, Rt 1.01 min (2 minute run).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (20 ml) and sat. NaHCO3 aq sol
  2. customThe two phases were separated
  3. extractionthe aqueous phase was extracted again with EtOAc (20 ml)
  4. customThe phases were separated
  5. customdried (hydrophobic frit)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on silica using a cyclohexane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cc2bd74513f14406871f14bdc298388d
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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