Methanol → Methyl 1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 2272534Notes

Reaction equation

HRID 2272534 reaction equation
C(N(CC)CC)C.[CH3:8][OH:9].I[C:11]1[CH:16]=[CH:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[C:13](=[O:30])[C:12]=1[CH3:31].[C]=O.CN([CH:37]=[O:38])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([N:14]2[CH:15]=[CH:16][C:11]([C:8]([O:38][CH3:37])=[O:9])=[C:12]([CH3:31])[C:13]2=[O:30])[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 118037690Tert-butyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylateHCID 178418416HCID 178418416, compound

Product 1

HCID 118037713Methyl 1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (II) (416 mg), triethylamine (1.59 mL) and methanol (6.91 mL) was added to a solution of tert-butyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylate (2.38 g) in DMF (15 mL) at room temperature. The mixture was stirred at 90 C under 0.5 MPa of carbon monoxide atmosphere for 7 hours. The mixture was quenched with water at room temperature and filtrated through celite. The filtrate was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was passed through a silica gel (NH, hexane/ethyl acetate) and concentrated in vacuo. The residue was triturated with diisopropyl ether/hexane and collected by filtration to give the title compound (1.77 g).

Workup

  1. customThe mixture was quenched with water at room temperature
  2. filtrationfiltrated through celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diisopropyl ether/hexane
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f8bcf13ad9ac4dab8b3ba9d71ad87d0d
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

Loading…