Allyl bromide → HCID 68555530, compound

HRID 2382103Notes

Reaction equation

HRID 2382103 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1([Cl:14])[CH:13]=[CH:12][CH:11]=[N:10][CH2:9]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([Cl:14])[CH:13]=[CH:12][CH:11]=[N:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 68557507HCID 68557507, compound

Product 1

HCID 68555530HCID 68555530, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (8.4 g, 36.8 mmol), allyl bromide (7.46 g, 39.1 mmol) and cesium carbonate (24.9 g, 76.4 mmol) in DMF (100 mL) is heated at 600 C. for 1 h. The reaction is quenched with water, extracted with EtOAc. The organic layer is dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-40% EtOAc in heptane to afford allyl-(3-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (8.4 g, 85%). MS: 269 (M+H); 1H NMR (300 MHz, CDCl3): δ=8.66 (s, 1H), 8.49 (d, 1H), 7.18 (d, 1H), 5.80-5.96 (m, 1H) 5.15 (s, 1H), 5.10(d, 1H), 4.2 (broad s, 1H), 1.43 (s, 9H).

Workup

  1. temperatureis heated at 600 C
  2. customThe reaction is quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 0-40% EtOAc in heptane

Sources & evidence

ORD record
ord-b0b58e73a4224154b41981ec4f49bd9d
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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