Ethyl{[6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl]oxy}acetate → Ethyl 3-amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridine-2-carboxylate

HRID 8820Notes

Reaction equation

HRID 8820 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[N:8]=1)[CH3:2].C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+]>CN(C=O)C.C1COCC1>[NH2:14][C:13]1[C:12]2[C:7](=[N:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH:11]=2)[O:6][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:29]

Participants

5

Reactant 2

HCID 21984952Ethyl{[6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl]oxy}acetateHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 21984925Ethyl 3-amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred solution of 2.69 g (6.30 mmol) of the product of Step A dissolved in 60 mL of DMF was slowly added 12.6 mL of a 1 M solution of lithium bis(trimethylsilylamide) in THF at 0° C. The reaction mixture was stirred at room temperature for 20 min then partitioned between EtOAc and 10% aq. NaHSO4. The organic extracts were separated, washed with 10% aq. NaHSO4, brine, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 427.0 (M+1), 428.9 (M+3); Rt=4.03 min.

Workup

  1. customat 0° C
  2. customthen partitioned between EtOAc and 10% aq. NaHSO4
  3. customThe organic extracts were separated
  4. washwashed with 10% aq. NaHSO4, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 0–20% EtOAc-hexane
  10. customEvaporation of the purified fractions
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-0072402313da45f9b61c45596ccdd4e7
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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