Pyridine → HCID 60004116, compound

HRID 2183460Notes

Reaction equation

HRID 2183460 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].Cl[C:19]1[CH:24]=[N:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>C(Cl)Cl.[Cu](I)I.CCOC(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[CH:11]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 73277ChloropyrazineHCID 56971802Tert-butyl [(1S)-1-(3-hydroxyphenyl)ethyl]carbamate

Product 1

HCID 60004116HCID 60004116, compoundYield 113.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of (S)-[1-(3-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (1 g, 4.2 mmol), 2-chloro-pyrazine (0.58 g, 5.1 mmol), potassium carbonate (powder, 1.4 g, 10.1 mmol), copper iodide (325 mesh powder, 0.6 g, 3.2 mmol) and pyridine (5 mL) was heated at 115° C. for 24 h. CH2Cl2 (100 mL) was added, and the reaction mixture was diluted with CH2Cl2 (100 mL), filtered through celite, and rinse with CH2Cl2 (2×50 mL). The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel eluting with 1:1/Hexane:EtOAc to give the title product (1.5 g, quantitative yield).

Workup

  1. filtrationfiltered through celite
  2. washrinse with CH2Cl2 (2×50 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel eluting with 1:1/Hexane

Sources & evidence

ORD record
ord-e43d0d9217cf42f3ab7ec4e3dc552667
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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