Ethyl 4-piperidinecarboxylate → HCID 59318148, compound

HRID 2190572Notes

Reaction equation

HRID 2190572 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[O:7])=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[NH:28]1[CH2:38][CH2:37][CH:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:30][CH2:29]1>O1CCOCC1.CN(C1C=CN=CC=1)C>[CH2:35]([O:34][C:32]([CH:31]1[CH2:37][CH2:38][N:28]([C:2]2[CH:18]=[CH:17][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=3[F:16])=[CH:4][N:3]=2)[CH2:29][CH2:30]1)=[O:33])[CH3:36]

Participants

6

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 81531DiisopropylethylamineHCID 59318151HCID 59318151, compound

Product 1

HCID 59318148HCID 59318148, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

6-Chloro-N-(2-fluoro-4-iodo-phenyl)-nicotinamide (80 mg, 0.22 mmol) was dissolved in dioxane (6 mL) and the mixture was treated with diisopropyl ethyl amine (0.11 mL, 0.66 mmol), ethyl isonipecotate (100 mg, 0.66 mmol) and a catalytic amount of DMAP. This solution was then heated in a sealed tube at 95° C. for 21 h. The mixture was then cooled and the solvent was evaporated. The residue was chromatographed with a silica gel column and 20-40% EtOAc in hexanes gradient to afford the product. (60 mg, Yield: 55%)

Workup

  1. temperatureThe mixture was then cooled
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed with a silica gel column and 20-40% EtOAc in hexanes gradient
  4. customto afford the product

Sources & evidence

ORD record
ord-ef639cbc6e7c409f81fd67d9f0341a44
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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