Thiomorpholine 1,1-dioxide → 5-(1,1-Dioxo-thiomorpholin-4-yl)methyl-2-phenyl-7-nitro-1H-indole

HRID 2089592Notes

Reaction equation

HRID 2089592 reaction equation
I[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:6]2.[O:21]=[S:22]1(=[O:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C1COCC1.O>[O:21]=[S:22]1(=[O:28])[CH2:27][CH2:26][N:25]([CH2:2][C:3]2[CH:4]=[C:5]3[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[NH:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6]3)[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 6484228Thiomorpholine 1,1-dioxideHCID 684702645-Iodomethyl-2-phenyl-7-nitro-1H-indole

Product 1

HCID 684718685-(1,1-Dioxo-thiomorpholin-4-yl)methyl-2-phenyl-7-nitro-1H-indoleYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Iodomethyl-2-phenyl-7-nitro-1H-indole (850 mg, 2.5 mmol) prepared in Step A was dissolved in THF (10 mL). 1,1-Dioxo-thiomorpholine (405 mg, 2.25 mmol) was added thereto, and the mixture was stirred for 2 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with EtOAc, dried over anhydrous magnesium sulfate, and filtered. The residue was recrystallized from DCM and hexane to give the title compound (625 mg, Yield 65%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe residue was recrystallized from DCM and hexane

Sources & evidence

ORD record
ord-513493ad091d4320a64d5224ba7010f9
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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