2-(Di-tert-butylphosphino)biphenyl → Ethyl 7-azetidin-1-yl-6-cyano-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696941Notes

Reaction equation

HRID 1696941 reaction equation
[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:24])[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][N:12]3[CH2:15][CH2:16][C:17]#[N:18])=[CH:7][C:6]=2Br)[CH2:4][CH2:3][CH2:2]1.[C:26]([Zn]C#N)#[N:27].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:24])[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][N:12]3[CH2:15][CH2:16][C:17]#[N:18])=[CH:7][C:6]=2[C:26]#[N:27])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 67275613Ethyl 7-azetidin-1-yl-6-bromo-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 178514179HCID 178514179, compound

Product 1

HCID 67274868Ethyl 7-azetidin-1-yl-6-cyano-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of EXAMPLE 82A (0.50 g), dicyanozinc (0.29 g), 2-(di-tert-butylphosphino)biphenyl (0.15 g), and tris(dibenzylideneacetone)dipalladium(0) (0.11 g) in acetonitrile (20 mL) was refluxed for 1 hour then cooled and filtered; and the filtrate was diluted with water and filtered.

Workup

  1. temperaturethen cooled
  2. filtrationfiltered
  3. additionand the filtrate was diluted with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e25cfb1e2fdc4573812b755d3fa4b071
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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