Cesium carbonate → N-(1-(4-Methoxyphenylsulfonyl)-2,3-dihydro-1H-indol-7-yl)isonicotinamide

HRID 18699

Reaction equation

HRID 18699 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.Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[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:23](=[O:30])[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 247482541-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-ylamine

Product 1

HCID 16215971N-(1-(4-Methoxyphenylsulfonyl)-2,3-dihydro-1H-indol-7-yl)isonicotinamideYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 19 (0.2 g, 0.52 mmol), isonicotinoyl chloride hydrochloride (0.18 g, 1.04 mmol), and cesium carbonate (0.68 g, 2.08 mmol) in acetonitrile (20 ml) was heated to reflux for 16 h. The reaction mixture was quenched with ice water and extracted with CH2Cl2. The combined organic layer was dried over MgSO4 and evaporated to give a residue that was purified by silica gel flash column chromatography (EtOAc:n-hexane :NH3(aq)=3:2:1%) and recrystallized (CH2Cl2/EtOAc) to afford compound 26, yield 82%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. customThe reaction mixture was quenched with ice water
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. customevaporated
  7. customto give a residue that
  8. customwas purified by silica gel flash column chromatography (EtOAc:n-hexane :NH3(aq)=3:2:1%)
  9. customrecrystallized (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-9cabd8ab2a684028b3e6a1d2de242f8c
Source dataset
uspto-grants-2010_06
Patent number
US07741495B2

Linked notes

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