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Pyridine → 7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbonitrile

HRID 1188877
Notes
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Reaction equation

HRID 1188877 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([NH2:20])=O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]#[N:20])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 668976427-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide

Product 1

HCID 668975217-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carbonitrileYield 92%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

To a mixture of 7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (840 mg), pyridine (0.23 mL) and N,N-dimethylformamide (20 mL) was added dropwise oxalyl chloride (0.25 mL) under ice-cooling, and the mixture was stirred for 2 hr. Pyridine (0.23 mL) and oxalyl chloride (0.25 mL) were successively added, and the mixture was further stirred for 30 min. Water was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was washed with a mixed solvent of diethyl ether-hexane to give the title compound (660 mg, yield 92%) as yellow crystals. The obtained yellow crystals were recrystallized from ethanol-hexane to give yellow crystals. melting point 209-210° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed successively with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe obtained solid was washed with a mixed solvent of diethyl ether-hexane

Sources & evidence

ORD record
ord-34cb040feda8427a8638daa28a4669b2
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673942B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes