Iodoethane → HCID 117992935, compound

HRID 922580Notes

Reaction equation

HRID 922580 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](I)[CH3:19]>CS(C)=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:18][CH3:19])=[C:4]([F:11])[CH:3]=1.[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH2:18][CH3:19])[CH:6]=2

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 247287446-Bromo-4-fluoro-1H-indazole

Product 2

HCID 117992935HCID 117992935, compoundYield 52%HCID 117992991HCID 117992991, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-bromo-4-fluoro-1H-indazole (1000 g, 4.65 mol) in DMSO (5.0 L), was added K2CO3 (900 g, 6.51 mol), followed by addition of ethyl iodide (900 g, 5.77 mol). The reaction mixture was stirred at r.t. for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes) to give 6-bromo-1-ethyl-4-fluoro-1H-indazole (595 g, 2.45 mol, 52%) as a yellow oil and 6-bromo-2-ethyl-4-fluoro-2H-indazole (278 g, 1.14 mol, yield 17%) as an orange solid. 1H NMR (600 MHz, CDCl3) δ 1.52 (t, 3H), 4.39 (q, 2H), 6.95 (dd, 1H), 7.40 (s, 1H), 8.02 (s, 1H). MS (ES+)(M+H) 243.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-076eb262a5ab47c4996e9acdc0648546
Source dataset
uspto-grants-2016_03
Patent number
US09278953B2

Reaction notes

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