Methanol → HCID 118037562, compound

HRID 2272457Notes

Reaction equation

HRID 2272457 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:4](=[O:21])[CH:3]=1.C(N(CC)CC)C.[CH3:29][OH:30].[C]=O.CN([CH:36]=[O:37])C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]([N:5]2[CH:6]=[CH:7][C:2]([C:29]([O:37][CH3:36])=[O:30])=[CH:3][C:4]2=[O:21])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 118037923HCID 118037923, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 118037562HCID 118037562, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

A mixture of tert-butyl 4-(4-bromo-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylate (14.7 g), triethylamine (11.5 mL), methanol (50 mL), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (3.01 g), and DMF (137 mL) was stirred at 80 C for 4 hours in a carbon monooxide atmosphere of 0.3 MPa. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with saturated saline twice and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) and silica gel column chromatography (NH, hexane/ethyl acetate) to obtain the title compound (8.32 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe obtained organic layer was washed with saturated saline twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) and silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-464b520c007d45b58b9571e8809b1e34
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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