Water → HCID 58086157, compound

HRID 1964873Notes

Reaction equation

HRID 1964873 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[N:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[CH2:15]([S:18]([NH:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])(=[O:20])=[O:19])[CH2:16][CH3:17].O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]2[C:9]([C:25]([C:24]3[CH:23]=[C:22]([NH:21][S:18]([CH2:15][CH2:16][CH3:17])(=[O:20])=[O:19])[CH:30]=[CH:29][CH:28]=3)=[O:26])=[CH:10][NH:11][C:12]2=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 58087452HCID 58087452, compound

Product 1

HCID 58086157HCID 58086157, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To aluminum trichloride (4.8 g, 36.0 mmol) in methylene chloride (70.0 mL), under an atmosphere of nitrogen, was added 5-bromo-1H-pyrrolo[2,3-b]pyridine (67, 797 mg, 4.04 mmol) dissolved in methylene chloride (5.0 mL). The reaction was stirred at room temperature for 30 minutes, followed by addition of 3-(propane-1-sulfonylamino)-benzoyl chloride (77, 1.10 g, 4.20 mmol) dissolved in methylene dichloride (4.0 mL). The reaction was stirred at room temperature for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (P-1116, 300.0 mg). MS(ESI) [M−H+]−=420.1, 422.1.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexane
  8. customto give a white solid (P-1116, 300.0 mg)

Sources & evidence

ORD record
ord-f066a3d02edf426cb4bfe81997a135d8
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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