1-Bromo-3-chloropropane → HCID 58900128, compound

HRID 2242862Notes

Reaction equation

HRID 2242862 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.BrC[CH2:21][CH2:22][Cl:23].C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C.O>[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:21][CH2:22][Cl:23])=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 2776908HCID 2776908, compound

Product 1

HCID 58900128HCID 58900128, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The title compound was prepared from 3-chloro-2-(4-methoxy-phenyl)-2H-indazole (1.2 g, 4.9 mmol) and 1-bromo-3-chloropropane (3.1 g, 19.6 mmol), K2CO3 (2.8 g, 20.4 mmol), in methyl ethyl ketone (50 mL) was refluxed for 36 h. After the reaction mixture was diluted with water, the resulting aqueous mixture was extracted with ethyl acetate and sequentially washed with water, saturated aq. NaHCO3, water and brine. The combined organic portions were dried over Na2 SO4, filtered and concentrated in vacuo to afford the title compound (1.2 g, 80%). MS (APCI) m/z: 321 (M+1, 100).

Workup

  1. temperaturewas refluxed for 36 h
  2. extractionthe resulting aqueous mixture was extracted with ethyl acetate
  3. washsequentially washed with water, saturated aq. NaHCO3, water and brine
  4. customThe combined organic portions were dried over Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5a93d77689e4c5aa94f4806bc951ac6
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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