Potassium Carbonate → 3-[3-(5-Bromo-1-methyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747450Notes

Reaction equation

HRID 1747450 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2].[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([CH2:31][N+](C)(C)C)[CH:30]=1)[N:27]([CH3:36])[CH:26]=[CH:25]2.[I-].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:31][C:29]2[CH:30]=[C:22]([Br:21])[CH:23]=[C:24]3[C:28]=2[N:27]([CH3:36])[CH:26]=[CH:25]3)[C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497279HCID 59497279, compound

Product 1

HCID 594976003-[3-(5-Bromo-1-methyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl esterYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester (50 mg, 0.18 mmol) in DMF (10 mL) were added (5-Bromo-1-methyl-1H-indol-7-ylmethyl)-trimethyl-ammonium; iodide (111 mg, 0.27 mmol) and K2CO3 (75 mg, 0.54 mmol) at room temperature under nitrogen atmosphere. The solution was heated to 100 C for 2 hours. The solution was cooled down and water was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The solution was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product 3-[3-(5-Bromo-1-methyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (50 mg, 55%) as a colorless foam.

Workup

  1. customat room temperature
  2. temperatureThe solution was heated to 100 C for 2 hours
  3. temperatureThe solution was cooled down
  4. extractionThe solution was extracted with EtOAc
  5. dry with materialthe combined organic layer was dried with MgSO4
  6. filtrationThe solution was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-bc5a465a724d4a21aaf94d7596d91cb7
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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