2-Bromopyridine → HCID 60004110, compound

HRID 2183455Notes

Reaction equation

HRID 2183455 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].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>[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]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:11]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 56971802Tert-butyl [(1S)-1-(3-hydroxyphenyl)ethyl]carbamate

Product 1

HCID 60004110HCID 60004110, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of (S)-[1-(3-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (10 g, 42.1 mmol), 2-bromopyridine (8 g, 50.6 mmol), potassium carbonate (powder, 14 g, 101 mmol) and copper iodide (325 mesh powder, 6 g, 31.6 mmol) was heated at 115° C. for 12 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. CH2Cl2 (100 mL) was added, and the resulting reaction mixture was filtered. The filtrate was washed with H2O (3×50 mL) followed by brine (100 ml), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 2:1/Hexane:EtOAc to give the title product (12.1 g, 91% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionCH2Cl2 (100 mL) was added
  4. customthe resulting reaction mixture
  5. filtrationwas filtered
  6. washThe filtrate was washed with H2O (3×50 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel eluting with 2:1/Hexane

Sources & evidence

ORD record
ord-09292a299bb74ba98125b6486a69d1a9
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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