HCID 58961588, compound → HCID 10309568, compound

HRID 916945Notes

Reaction equation

HRID 916945 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:3]=1>CO.C(OCC)(=O)C.[Pd]>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:4]1[N:3]=[CH:2][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

5

Reactant 1

HCID 58961588HCID 58961588, compound

Product 1

HCID 10309568HCID 10309568, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-chloro-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate (750 mg, 1.76 mmol) from Step A in methanol (10 mL) and ethyl acetate (10 mL) was added 10% Pd/C (100 mg). The suspension was stirred under an atmosphere of hydrogen (balloon pressure) for 45 min and was then filtered to remove the catalyst. HPLC/MS indicated a mixture of starting material, desired product, and minor amounts of several possible phenyl ring dechlorination products. The filtrate was evaporated and the residue was purified by flash column chromatography on silica gel eluted with 5 to 20% ethyl acetate in hexanes. The fractions containing the title compound were repurified by preparative TLC eluted with 15% ethyl acetate in hexanes to give pure methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate. HPLC/MS: 392 (M+1), 394 (M+3); Rt=4.29 min. 1HNMR (CDCl3): δ 4.024 (s, 3H), 7.11 (br d, J=8.6 Hz, 2H), 7.23-7.35 (m, 4H), 7.36 (d, J=2.0 Hz, 1H), 7.37 (d, J=1.9 Hz,, 1H), 9.286 (d, J=1.9 Hz, 1H).

Workup

  1. filtrationwas then filtered
  2. customto remove the catalyst
  3. additiona mixture of starting material, desired product, and minor amounts of several possible phenyl ring dechlorination products
  4. customThe filtrate was evaporated
  5. customthe residue was purified by flash column chromatography on silica gel
  6. washeluted with 5 to 20% ethyl acetate in hexanes
  7. additionThe fractions containing the title compound
  8. customwere repurified by preparative TLC
  9. washeluted with 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-31e03fb6b2714820bd1bb7bb2e4a5fd2
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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