Allyl bromide → HCID 86639381, compound

HRID 2382093Notes

Reaction equation

HRID 2382093 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:15])[N:7]([CH2:18][CH:17]=[CH2:16])[C:8]1[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 11961738tert-Butyl (2-chloropyridin-3-yl)carbamate

Product 1

HCID 86639381HCID 86639381, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (2-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (7 g, 30.7 mmol), allyl bromide (5.26 g, 40.8 mmol) and cesium carbonate (20.8 g, 63.8 mmol) in DMF (280 mL) is heated at 60° C. for 1 h. The reaction is quenched with water, extracted with EtOAC. The organic layer is dried (Na2SO4), filtered and concentrated to afford allyl-(2-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (8.03 g, 98%), which is sued in the next step with no further purification.

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted with EtOAC
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-999b89c3fe3845049d78839f8e108d36
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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