Iodoethane → HCID 74889420, compound

HRID 922583Notes

Reaction equation

HRID 922583 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([CH3:11])[CH:3]=1.[OH-].[Na+].[CH2:14](I)[CH3:15]>C1COCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:14][CH3:15])=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 247287706-Bromo-4-methyl-1H-indazole

Product 1

HCID 74889420HCID 74889420, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-4-methyl-1H-indazole (1000 mg, 4.7 mmol) in THF (15 mL) was added sodium hydroxide (474 mg, 11.8 mmol) and tetrabutylammonium hydrogen sulfate (80.5 mg, 0.24 mmol). The reaction mixture was stirred at r.t. for 1 h and then treated with ethyl iodide (887 mg, 5.7 mmol) dropwise. The resulting mixture was stirred at r.t. overnight. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (0-100% EtOAc in heptane) to afford 6-Bromo-1-ethyl-4-methyl-1H-indazole (476 mg, 42%). 1H NMR (600 MHz, CDCl3) δ 1.51 (t, 3H), 2.57 (s, 3H), 4.38 (q, 2H), 7.04-7.06 (m, 1H), 7.43 (s, 1H), 7.97 (d, 1H). MS (AP+)(M+H) 239.

Workup

  1. stirringThe resulting mixture was stirred at r.t. overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-013d71be2ffe495595932761fcf7da4d
Source dataset
uspto-grants-2016_03
Patent number
US09278953B2

Reaction notes

Loading…