Sodium Iodide → HCID 49833748, compound

HRID 1614862Notes

Reaction equation

HRID 1614862 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C@H:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[CH:5][CH:4]=1.[Na+].[I-].Cl[Si](C)(C)C.OS([O-])=O.[Na+]>C(#N)C.C(Cl)Cl>[O:14]=[C:11]1[CH2:12][CH2:13][C@H:9]([C:6]2[CH:5]=[CH:4][C:3](=[O:2])[NH:8][CH:7]=2)[CH2:10]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 23665763Sodium BisulfiteHCID 49833565HCID 49833565, compound

Product 1

HCID 49833748HCID 49833748, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

(3S)-3-(6-methoxy-3-pyridyl)cyclopentanone (preparation 3) (560 mg, 2.9 mmol) was dissolved in acetonitrile (12 mL) and treated with NaI (1.32 g, 8.8 mmol) followed by chlorotrimethylsilane (0.74 mL, 5.9 mmol). The reaction mixture was heated in a microwave reactor at 100° C. for 5 min. Following the addition of DCM and aqueous NaHSO3, the mixture was washed with water. The organic phase was dried over MgSO4 and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, DMSO) δ 11.43 (s, 1H), 7.50 (dd, 1H), 7.19 (d, 1H), 6.32 (d, 1H), 3.21-3.06 (m, 1H), 2.46-2.35 (m, 1H), 2.33-2.11 (m, 4H), 1.90-1.69 (m, 1H).

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdd11e4a755c4198a40ef2c5174e1e4f
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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