Benzoyl chloride → N-[1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-yl]-benzamide

HRID 18698Notes

Reaction equation

HRID 18698 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[NH2:21])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 247482541-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-ylamine

Product 1

HCID 25168005N-[1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-yl]-benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 19(0.1 g, 0.26 mmol), benzoyl chloride (0.09 ml, 0.78 mmol) in pyridine (1 ml) was stirred at 100-110° C. for 16H. The reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4 and evaporated to give residue that was chromatographed over silica gel (EtOAc: n-hexane=1:2) to afford 20, yield 82%.

Workup

  1. customThe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. customevaporated
  5. customto give residue that
  6. customwas chromatographed over silica gel (EtOAc: n-hexane=1:2)

Sources & evidence

ORD record
ord-42ca22a9aa3346ec9515737ca0d3a6e8
Source dataset
uspto-grants-2010_06
Patent number
US07741495B2

Reaction notes

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