Triethylamine → HCID 86674888, compound

HRID 1184694Notes

Reaction equation

HRID 1184694 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](I)[C:5]([OH:9])=[CH:4][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.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[O:9][C:5]3[C:6](=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylateHCID 234331586-Chloro-2-iodo-3-hydroxypyridine

Product 1

HCID 86674888HCID 86674888, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-chloro-2-iodo-pyridin-3-ol (1.00 g) in N,N-dimethylformamide (10 mL) copper (I) iodide (120 mg), Pd(PPh3)2Cl2 (140 mg), and triethylamine (550 μL) are added. The mixture is stirred at room temperature for 1 h. A solution of 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (860 mg) in N,N-dimethylformamide (3 mL) is added and the resulting mixture is stirred at 70° C. over night. After cooling to room temperature the mixture is concentrated and chromatographed on silica gel (ethyl acetate/cyclohexane 25:75) to give the title compound. Yield: 241 mg (18% of theory); LC (method 2): tR=1.41 min; Mass spectrum (ESI+): m/z=337 [M+H]+.

Workup

  1. stirringthe resulting mixture is stirred at 70° C. over night
  2. temperatureAfter cooling to room temperature the mixture
  3. concentrationis concentrated
  4. customchromatographed on silica gel (ethyl acetate/cyclohexane 25:75)

Sources & evidence

ORD record
ord-e3213d408eed458cbfaa3456d1c02a9d
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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