Benzoyl chloride → HCID 25213946, compound

HRID 2089578Notes

Reaction equation

HRID 2089578 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:17])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[CH:7]2.CCN(CC)CC.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.O>[CH3:17][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:3]=1)[NH:9][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[CH:7]2

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68474590HCID 68474590, compound

Product 1

HCID 25213946HCID 25213946, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7-Amino-5-methyl-2-(pyridin-2-yl)-1H-indole (45 mg, 0.20 mmol) prepared in Step A of Example 1 was dissolved in dichloromethane (10 mL). Et3N (0.56 mL, 0.4 mmol) and benzoyl chloride (0.03 mL, 0.22 mmol) were added thereto, and the mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was diluted with water, extracted with EtOAc, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (eluent EtOAc/n-Hex=1/5) to give the title compound (18 mg, Yield 27%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (eluent EtOAc/n-Hex=1/5)

Sources & evidence

ORD record
ord-1236e8737cc14780abf8424a86132100
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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