Ethanol → HCID 11526473, compound

HRID 552315Notes

Reaction equation

HRID 552315 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:27])=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25]I)[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:28])=[CH:10]2)=[C:4]([CH3:29])[CH:3]=1.[O-:30][S:31]([O-:33])=[O:32].[Na+].[Na+].C(O)C.O1CCCC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:27])=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][S:31]([OH:33])(=[O:32])=[O:30])[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:28])=[CH:10]2)=[C:4]([CH3:29])[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 58281259HCID 58281259, compound

Product 1

HCID 11526473HCID 11526473, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-(4-bromo-2,6-dimethyl-phenyl)-4-[4-(2-iodo-ethyl)-piperidin-1-yl]-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridine (0.25 g), Na2SO3 (0.28 g), tetrabutylammonium iodide (16 mg), ethanol (5 mL), tetrahydrofuran (5 mL) and water (3 mL) was heated at reflux for 10 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: ethyl acetate:methanol=5/1) to obtain the title compound (56 mg) as a yellow amorphous.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: ethyl acetate:methanol=5/1)

Sources & evidence

ORD record
ord-374eb53b9a96408ca6efae223bcb7aa1
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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