Potassium Carbonate → HCID 69080174, compound

HRID 1916656Notes

Reaction equation

HRID 1916656 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[C:20]([O-])([O-:22])=[O:21].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:20]([O:22][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:21])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2×HCID 34115665-Bromoindoline

Product 1

HCID 69080174HCID 69080174, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1.00 g (4.95 mmol) 5-bromoindoline is added to a solution of 868 mg (5.00 mmol) N-(2-chloroethyl)-pyrrolidine hydrochloride and 1.70 g (12.2 mmol) K2CO3 in 15 mL DMF. The reaction solution is stirred for 4 h at 70° C. and more N-(2-chloroethyl)-pyrrolidine hydrochloride is added. The reaction solution is stirred for a further 3 h at 70° C. and then diluted with 25 mL water. The aqueous phase is extracted twice with 30 mL EtOAc. The organic phase is washed with saturated NaCl solution, dried over Na2SO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (gradient: EtOAc/MeOH 9:1 to EtOAc/MeOH 4:1).

Workup

  1. stirringThe reaction solution is stirred for a further 3 h at 70° C.
  2. extractionThe aqueous phase is extracted twice with 30 mL EtOAc
  3. washThe organic phase is washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customThe purification

Sources & evidence

ORD record
ord-b6a286b2e54649f4aef97bd1bf9cfd99
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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