Triethylamine → 2-Bromo-1-[(3SR,4RS)-3-[(RS)-1 (5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-ethanone

HRID 1158652Notes

Reaction equation

HRID 1158652 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([CH:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:14][NH:13][CH2:12]2)[CH3:10])=[N:6][CH:7]=1.CCN(CC)CC.[Br:31][CH2:32][C:33](Cl)=[O:34]>C(Cl)Cl>[Br:31][CH2:32][C:33]([N:13]1[CH2:14][CH:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH:11]([CH:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)[CH3:10])[CH2:12]1)=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 669991845-Chloro-2-{(RS)-1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-pyridine

Product 1

HCID 673278832-Bromo-1-[(3SR,4RS)-3-[(RS)-1 (5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-ethanoneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-chloro-2-{(RS)-1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-pyridine (XV-B-2) 0.12 g (0.32 mmol) in CH2Cl2 (10 mL) at RT, 0.055 ml (0.38 mmol) of Et3N and 0.032 mL (0.33 mmol) of bromo-acetyl chloride were added. Stirring was continued over night and then concentrated under vacuo. The crude residue was dissolved in EtOAc, washed with H2O. The organic phase was dried over Na2SO4 and the product was purified by flash chromatography (SiO2, EtOAc) to yield the title product 0.15 g (92%) as a colorless oil.

Workup

  1. waitwas continued over night
  2. concentrationconcentrated under vacuo
  3. dissolutionThe crude residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe product was purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-0b41f73d77e546c3b71802085483bd07
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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