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Water → 1-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indole

HRID 1890364
Notes
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Reaction equation

HRID 1890364 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[F:13][CH:14]([F:26])[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>CN(C)C=O>[F:26][CH:14]([F:13])[O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:24])=[O:23])=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27782234-(Difluoromethoxy)benzenesulfonyl chlorideHCID 27823135-Iodo-1H-indole

Product 1

HCID 685969371-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indoleYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Conditions

Temperature
0 °C

Procedure

5-Iodo-1H-indole (2.0 g, 8.23 mmol) was dissolved in dimethylformamide (DMF) (10 ml) and cooled to 0° C. Sodium hydride (494 mg, 12.34 mmol) was added in small portions. The reaction mixture was stirred for 1 hour at 0° C. 4-(Difluoro-methoxy)-benzenesulfonyl chloride (2.196 g, 9.05 mmol) was dissolved in DMF (5 ml), and added slowly to the reaction mixture. Stirring was continued for 45 minutes. Cold water (150 ml) was added to the reaction mixture. The reaction mixture was extracted twice with ethyl acetate (100 ml). The organic layer was dried over magnesium sulphate, filtered, and the solvent evaporated under reduced pressure to give a crystalline solid (3.0 g, 81%). ESI-MS [m/z]: 449.95 [M+H]+. 1H-NMR (500 MHz, d6-DMSO): δ=8.05 (d, 2H), 8.0 (s, 1H), 7.85 (d, 1H), 7.8 (d, 1H), 7.65 (d, 1H), 7.4 (t, J=70 Hz, 1H), 7.35 (d, 2H), 6.8 ppm (d, 1H).

Workup

  1. additionadded slowly to the reaction mixture
  2. stirringStirring
  3. waitwas continued for 45 minutes
  4. extractionThe reaction mixture was extracted twice with ethyl acetate (100 ml)
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-f769e013773543daa41273c834202e0a
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507469B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes