Ethyl 4-({6-[(dimethylamino)carbonyl]-1-oxidopyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate → Ethyl 4-({6-[(dimethylamino)carbonyl]pyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate

HRID 1177274Notes

Reaction equation

HRID 1177274 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N+:10]([O-])=[CH:9][C:8]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=2)=[CH:7][CH:6]=1)=[O:4]>C(O)(=O)C.[Fe]>[CH3:28][N:2]([CH3:1])[C:3]([C:5]1[N:10]=[CH:9][C:8]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 59560221Ethyl 4-({6-[(dimethylamino)carbonyl]-1-oxidopyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate

Product 1

HCID 59559976Ethyl 4-({6-[(dimethylamino)carbonyl]pyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of ethyl 4-({6-[(dimethylamino)carbonyl]-1-oxidopyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate (176 mg, 0.457 mmol) in 15 mL of acetic acid, was added powdered Fe while keeping the temperature at 70° C. for 2 hrs. LC-MS showed that the reaction was complete. The reaction was cooled to room temperature, and the insoluble material was filtered. The mother liquor was diluted with EtOAc, washed with NaHCO3, brine, and dried over Na2SO4, and concentrated. The crude product was introduced into a silica gel column and eluted with MeOH/CHCl3 (2/98 to 5/95) to provide the product (135 mg, 85% yield) as colorless oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.40 (t, J=7.16 Hz, 3 H) 2.47 (s, 3 H) 3.15 (d, 6 H) 4.39 (q, J=7.03 Hz, 2 H) 6.25 (s, 1 H) 7.30 (d, J=2.45 Hz, 1 H) 7.55-7.64 (m, 1 H) 7.64-7.76 (m, 1 H) 8.00 (s, 1 H) 8.38 (s, 1 H); LC-MS (ESI)+m/z=369.00 (M+H)+.

Workup

  1. customat 70° C.
  2. customfor 2 hrs
  3. filtrationthe insoluble material was filtered
  4. additionThe mother liquor was diluted with EtOAc
  5. washwashed with NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. additionThe crude product was introduced into a silica gel column
  9. washeluted with MeOH/CHCl3 (2/98 to 5/95)

Sources & evidence

ORD record
ord-0b3ef70e5c9d4f0ebfcaf15f1043f365
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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