Ethanol → (2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-[4-(pyridin-4-ylmethoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

HRID 1349568Notes

Reaction equation

HRID 1349568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].BrC[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1.C(O)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:37]4[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=4)=[CH:27][CH:28]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 6427994-(Bromomethyl)pyridineHCID 10343669N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 10324580(2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-[4-(pyridin-4-ylmethoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The phenol was dissolved in DMF (5 mL) at room temperature. Sodium hydride (60% in oil) was added and the mixture allowed to stir 30 min. 4-Bromomethyl-pyridine was added and the reaction was allowed to stir over night. Ethanol was added and the reaction was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (2/98 methanol/dichloromethane—5/95 methanol/dichloromethane gradient) to afford the product.

Workup

  1. stirringto stir over night
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. customThe crude residue was purified by silica gel chromatography (2/98 methanol/dichloromethane—5/95 methanol/dichloromethane gradient)
  9. customto afford the product

Sources & evidence

ORD record
ord-15bde44e0a1f4cc4ac6276eb7d0f0606
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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