Triethylamine → 4-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1471765Notes

Reaction equation

HRID 1471765 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4](I)[CH:3]=1.C(N(CC)CC)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]#[CH:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[O:8][C:5]3=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylateHCID 533020386-Chloro-4-iodopyridin-3-ol

Product 1

HCID 866748894-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Copper(I) iodide (25 mg) and bis-(triphenylphosphine)-palladium(II)-chloride (30 mg) are added to 6-chloro-4-iodo-pyridin-3-ol (200 mg) in N,N-dimethylformamide (3 mL) under Ar atmosphere at room temperature. Triethylamine (110 μL) is added and the resulting mixture is stirred at room temperature for 1 h. 4-Ethynyl-piperidine-1-carboxylic acid tert-butyl ester (175 mg) dissolved in N,N-dimethylformamide (2 mL) is added dropwise and the mixture is stirred at 55° C. for 3 h. The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30) to give the title compound. LC (method 2): tR=1.40 min; Mass spectrum (ESI+): m/z=337/339 (Cl) [M+H]+.

Workup

  1. additionis added dropwise
  2. stirringthe mixture is stirred at 55° C. for 3 h
  3. customThe solvent is evaporated
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30)

Sources & evidence

ORD record
ord-29e4a916bb2946cc940e75debc873a94
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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