Diiodomethane → HCID 11952183, compound

HRID 1669086Notes

Reaction equation

HRID 1669086 reaction equation
N(OC(C)(C)C)=O.[CH3:8][CH:9]1[CH2:23][C:22]2[C:11](=[CH:12][C:13]3[N+:18]([O-:19])=[N:17][C:16](N)=[N:15][C:14]=3[CH:21]=2)[CH2:10]1.[I:24]CI>C1COCC1.[Cu]I>[I:24][C:16]1[N:17]=[N+:18]([O-:19])[C:13]2[CH:12]=[C:11]3[C:22]([CH2:23][CH:9]([CH3:8])[CH2:10]3)=[CH:21][C:14]=2[N:15]=1

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 10906Tert-Butyl nitriteHCID 11952004HCID 11952004, compound

Product 1

HCID 11952183HCID 11952183, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl nitrite (2.5 mL, 18.6 mmol) was added a stirred mixture of amine 94 (1.30 g, 6.0 mmol), diiodomethane (4.8 mL, 60 mmol) and CuI (1.2 g, 6.3 mmol) in THF (50 mL) and the mixture stirred at reflux temperature for 3 h. The solution was cooled and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (20-50%) of EtOAc/pet. ether, to give chloride 100 (1.31 g, 67%) as a pale yellow solid: mp (EtOAc/pet. ether) 140-142° C.; 1H NMR δ 8.15 (s, 1H, H-9), 7.70 (s, 1H, H-5), 3.20-3.30 (m, 2H, CH2), 2.65-2.79 (m, 3H, H-7, CH2), 1.20 (d, J=6.4 Hz, 3H, CH3); 13C NMR δ 155.5, 149.9, 147.6, 133.4, 122.5, 121.7, 114.6, 41.3, 41.0, 35.0, 20.2. Anal. calcd for C11H10IN3O: C, 40.4; H, 3.1; N, 12.9. Found: C, 40.6; H, 3.0; N, 12.7%.

Workup

  1. temperatureat reflux temperature for 3 h
  2. temperatureThe solution was cooled
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography
  5. washeluting with a gradient (20-50%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-a86c969af6ab4c2290263c9223afb9d3
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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