1,2-Dichloroethane → HCID 86723172, compound

HRID 868886Notes

Reaction equation

HRID 868886 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[I:11].[Cl:12][CH2:13][CH2:14]Cl.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:12][CH2:13][CH2:14][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5]([I:11])=[N:6]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 178505475HCID 178505475, compound

Product 1

HCID 86723172HCID 86723172, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-fluoro-3-iodo-indazole (3.0 g, 11.5 mmol) and 1,2-dichloroethane (5.7 g, 57.3 mmol) in ACN (50 mL) was added K2CO3 (3.2 g, 22.9 mmol) at rt. The reaction was stirred overnight at reflux. The reaction mixture was filtered and concentrated in vacuo. Purification by silica gel chromatography (30:1:5 hexanes/EtOAc/DCM) gave 2.5 g (67%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 3.97 (2H, t, J=6.0 Hz), 4.69 (2H, t, J=6.0 Hz), 7.13 (1H, dd, J=1.8, 7.8 Hz), 7.22-7.29 (1H, m), 7.42 (1H, dd, J=3.9, 9.3 Hz).

Workup

  1. temperatureat reflux
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (30:1:5 hexanes/EtOAc/DCM)

Sources & evidence

ORD record
ord-d9c468ab6307478b99ff50d07945717f
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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