N-Iodosuccinimide → 2-(3,4-Dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole

HRID 2409529Notes

Reaction equation

HRID 2409529 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][C:17]([CH3:19])=[CH:18][N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C(=O)N([I:27])C(=O)C1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][C:17]([CH3:19])=[C:18]([I:27])[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667171682-(3,4-Dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 667169392-(3,4-Dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole (0.346 g, 1.257 mmol) was dissolved in DCM (4.2 mL), and NIS (0.283 mg, 1.257 mmol) was added. The reaction mixture was stirred at RT overnight, quenched with sat. aq. thiosulfate and extracted with DCM. The organic layers were combined and washed with sat. aq. NH4Cl, dried (MgSO4), filtered and concentrated. The residue was suspended in Et2O, and the solid was filtered off, washed with Et2O and dried in vacuo affording the desired product (brown solid (0.295 g, 58%). TLC (cyclohexane/EtOAc 1:1) Rf 0.46; HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.53 min, [M+H]+ m/z 402.0; 1H NMR (300 MHz, CDCl3) δ/ppm 7.37 (s, 1H), 7.32 (d, J=8.3, 1H), 6.86 (d, J=8.3, 1H), 3.91 (d, J=14.3, 6H), 2.31 (s, 3H).

Workup

  1. customquenched with sat. aq. thiosulfate
  2. extractionextracted with DCM
  3. washwashed with sat. aq. NH4Cl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationthe solid was filtered off
  8. washwashed with Et2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-4160baea027f4cb98e127b06f29bb18f
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

Loading…