Diiodomethane → HCID 25139486, compound

HRID 1669157Notes

Reaction equation

HRID 1669157 reaction equation
C([N+]([O-])=O)(C)(C)C.[N+:8]1([O-:22])[C:13]2[CH:14]=[C:15]3[CH2:20][CH2:19][O:18][C:16]3=[CH:17][C:12]=2[N:11]=[C:10](N)[N:9]=1.C(I)[I:24]>C1COCC1.[Cu]I>[I:24][C:10]1[N:9]=[N+:8]([O-:22])[C:13]2[CH:14]=[C:15]3[CH2:20][CH2:19][O:18][C:16]3=[CH:17][C:12]=2[N:11]=1

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 116722-Methyl-2-nitropropaneHCID 25140915HCID 25140915, compound

Product 1

HCID 25139486HCID 25139486, compoundYield 49%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
20 °C

Procedure

tert-BuNO2 (90%, 3.8 mL, 28.8 mmol) was added to a stirred solution of 1-oxide 204 (2.0 g, 9.8 mmol), CH2I2 (3.8 mL, 46.7 mmol) and CuI (1.87 g, 9.8 mmol) in THF (40 mL), and the mixture was stirred at reflux temperature for 7 h. The mixture was cooled to 20° C., the solvent was evaporated and the residue purified by chromatography, eluting with a gradient (2-10%) of MeOH/DCM, to give iodide 213 (1.50 g, 49%) as a pale yellow solid: mp 192-194° C.; 1H NMR δ 8.19 (t, J=1.6 Hz, 1H, H-9), 7.10 (s, 1H, H-5), 4.83 (t, J=8.4 Hz, 2H, H-7), 3.44 (dt, J=8.4, 1.6 Hz, 2H, H-8); 13C NMR δ 167.0, 150.4, 136.2, 123.3, 116.4, 105.8, 103.7, 73.4, 29.0; HRMS calcd for C9H6IN3O2(M+) m/z 314.9505, found 314.9501.

Workup

  1. temperatureat reflux temperature for 7 h
  2. customthe solvent was evaporated
  3. customthe residue purified by chromatography
  4. washeluting with a gradient (2-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-412c248321b742be9c0f2cce5f912ff5
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

Loading…