Water → 5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carbonitrile

HRID 1188887Notes

Reaction equation

HRID 1188887 reaction equation
[CH3:1][S:2]([C:5]1[CH:31]=[CH:30][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:18]=2)[NH:15][C:14]([C:27]([NH2:29])=O)=[CH:13]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].N1C(Cl)=NC(Cl)=NC=1Cl.O.C(OCC)(=O)C>CN(C)C=O.CCCCCC>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH2:20][CH:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:18]=2)[NH:15][C:14]([C:27]#[N:29])=[CH:13]3)=[CH:30][CH:31]=1)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 668985525-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxamide

Product 1

HCID 668983485-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carbonitrileYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxamide (250 mg) was dissolved in N,N-dimethylformamide (5 mL), cyanuric chloride (311 mg) was added under ice-cooling, and the mixture was stirred for 1 hr. Water was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=10:90-60:40, volume ratio) to give the title compound (240 mg, yield 100%) as a white solid. MS 445 (MH+).

Workup

  1. temperaturecooling
  2. extractionthe mixture was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude product

Sources & evidence

ORD record
ord-fbfdd637c1ef43afaefe713fb485cdf8
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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