1-Bromo-3-chloropropane → HCID 178418704, compound

HRID 11491Notes

Reaction equation

HRID 11491 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][Cl:30]>CN(C=O)C>[Cl:30][CH2:29][CH2:28][CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178418971HCID 178418971, compound

Product 1

HCID 178418704HCID 178418704, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 3-[(4-hydroxy-phenylamino)-methylene]-1,3-dihydro-indol-2-one (0.945 g, 3.75 mmol) in 20 mL DMF is treated with potassium carbonate (777 mg, 1.5 equiv.) and 1-bromo-3-chloropropane (1.1 equiv.). The reaction mixture is heated to 40° C. for 3 h. The reaction mixture is partitioned between EtOAc and water. The organic layer is collected and washed sequentially with H2O (1×), saturated aqueous NaHCO3 solution (1×), and brine (1×). The organic phase was dried and concentrated to give an oil. The oil was purified by preparative chromatography (silica gel; 1:1 EtOAc:hexane) to give the named compound as a yellow solid (711 mg, 58%).

Workup

  1. customThe reaction mixture is partitioned between EtOAc and water
  2. customThe organic layer is collected
  3. washwashed sequentially with H2O (1×), saturated aqueous NaHCO3 solution (1×), and brine (1×)
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe oil was purified by preparative chromatography (silica gel; 1:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-ba0f07da5b164eb392ee45a4e001eba6
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Reaction notes

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