Cesium fluoride → HCID 66761489, compound

HRID 561799Notes

Reaction equation

HRID 561799 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][N:8]([CH:16]1[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[F-].[Cs+].[CH2:23]([Sn](CCCC)(CCCC)CCCC)[CH:24]=[CH2:25]>C1COCC1>[CH2:25]([C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][N:8]([CH:16]1[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 90628AllyltributylstannaneHCID 66762093HCID 66762093, compound

Product 1

HCID 66761489HCID 66761489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution (0.13 M) of tert-butyl (5-bromo-2-chlorobenzyl)cyclopropylcarbamate from the previous step (1 eq.), Pd(PCy3)2 (0.05 eq.) and cesium fluoride (2.0 eq.) was added allyl tributylstannane (1.2 eq.). The resulting brown solution was heated at reflux for 8 h and then filtered through a pad of SiO2. The insolubles were rinsed further with ether and the filtrate was concentrated in vacuo to afford a brown semisolid. Purification of the crude product thus obtained by way of column chromatography (SiO2, Hex→90:10 (v/v) Hex:Et2O) afforded the title compound as a colorless oil.

Workup

  1. temperatureThe resulting brown solution was heated
  2. temperatureat reflux for 8 h
  3. filtrationfiltered through a pad of SiO2
  4. washThe insolubles were rinsed further with ether
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto afford a brown semisolid
  7. customPurification of the crude product
  8. customthus obtained by way of column chromatography (SiO2, Hex→90:10 (v/v) Hex:Et2O)

Sources & evidence

ORD record
ord-5f980837f33244be8a38063c4a1a4a8b
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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