Water → HCID 58281259, compound

HRID 552313Notes

Reaction equation

HRID 552313 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]([CH3:31])=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25]OS(C)(=O)=O)[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:32])=[CH:10]2)=[C:4]([CH3:33])[CH:3]=1.[Na+].[I-:35].O>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:31])=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][I:35])[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:32])=[CH:10]2)=[C:4]([CH3:33])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 58281269HCID 58281269, compound

Product 1

HCID 58281259HCID 58281259, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methanesulfonic acid 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethyl ester (0.70 g) and NaI (0.59 g) in acetone (14 mL) was heated at reflux for 3 hours. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=10/1) to obtain 1-(4-bromo-2,6-dimethyl-phenyl)-4-[4-(2-iodo-ethyl)-piperidin-1-yl]-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridine (0.65 g) as a white crystal.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=10/1)

Sources & evidence

ORD record
ord-acb4d97e44d6475592182e9fe2f9800d
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

Loading…