Water → HCID 58281269, compound

HRID 552312Notes

Reaction equation

HRID 552312 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][OH:26])[CH2:20][CH2:19]4)=[C:12]3[C:11]([CH3:28])=[CH:10]2)=[C:4]([CH3:29])[CH:3]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32].N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[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[CH2:19][CH2:20][CH:21]([CH2:24][CH2:25][O:26][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:22][CH2:23]4)=[C:12]3[C:11]([CH3:28])=[CH:10]2)=[C:4]([CH3:29])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10253531HCID 10253531, compound

Product 1

HCID 58281269HCID 58281269, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol (0.93 g), which was prepared in the similar method as shown in example 1, in CHCl3 (10 mL), was added methanesulfonyl chloride (0.47 g) and pyridine (0.64 g) and the mixture was stirred at room temperature for 3 hours. Water was added into the reaction mixture and the mixture was extracted with CHCl3. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to obtain a brown oil. The oily product was crystallized from diisopropylether to obtain 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 (1.0 g).

Workup

  1. extractionthe mixture was extracted with CHCl3
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a brown oil
  7. customThe oily product was crystallized from diisopropylether

Sources & evidence

ORD record
ord-a6ec605f091940728164c6629b5cd240
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

Loading…