Ethyl pyridine-4-acetate → 3-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

HRID 896683Notes

Reaction equation

HRID 896683 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH:24]([C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1)[C:25]1[CH:26]=[C:27]([C:31]2[CH:32]=[C:33]([CH:41]([CH3:43])[CH3:42])[CH:34]=[C:35]3[C:40]=2[N:39]=[CH:38][CH:37]=[CH:36]3)[CH:28]=[CH:29][CH:30]=1>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.[Cl-].[NH4+].C(OCC)(=O)C>[CH2:11]([O:10][C:8](=[O:9])[CH:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[CH:24]([C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:32]=[C:33]([CH:41]([CH3:43])[CH3:42])[CH:34]=[C:35]3[C:40]=2[N:39]=[CH:38][CH:37]=[CH:36]3)[CH:26]=1)[CH3:12]

Participants

7

Reactant 3

HCID 736321Ethyl pyridine-4-acetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 223501108-{3-[Chloro-(4-chloro-phenyl)-methyl]-phenyl}-6-isopropyl-quinoline

Product 1

HCID 208149663-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolventHCID 86583969tetrahydrofuran HMPASolvent

Conditions

Temperature
21 °C

Procedure

To a solution of ethyl 4-pyridinylacetate (1.28 g, 7.74 mmol) in THF/HMPA (3:1, 5 mL) at −10° C. was added NaHMDS (1M, 7.8 mL, 7.8 mmol) dropwise. After 60 min., the crude chloride from Step 2 above was added and the resulting reaction mixture was stirred for 18 h at 21° C., and then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d6d57069dc714e23b79b60f542161d26
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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