Water → HCID 68809622, compound

HRID 656927Notes

Reaction equation

HRID 656927 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[CH:13]=[CH:12][C:11](=[O:17])[N:10]([CH2:18][CH:19]=[CH2:20])[C:9]=2[N:8]=1)(=O)=O.O.[CH3:24][N:25](C=O)C>[C-]#N.[C-]#N.[Zn+2].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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:17]=[C:11]1[N:10]([CH2:18][CH:19]=[CH2:20])[C:9]2[N:8]=[C:7]([C:24]#[N:25])[CH:16]=[CH:15][C:14]=2[CH:13]=[CH:12]1

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 86635318HCID 86635318, compound

Product 1

HCID 68809622HCID 68809622, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×

Conditions

Temperature
50 °C

Procedure

To a degassed solution of 7-oxo-8-(2-propen-1-yl)-7,8-dihydro-1,8-naphthyridin-2-yl trifluoromethanesulfonate (697 mg, 2.087 mmol) in DMF (10 ml) was added Zn(CN)2, (147 mg, 1.252 mmol) Pd2(dba)3 (48 mg, 0.052 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (58 mg, 0.104 mmol). The reaction was then heated at 50° C. for 1 h and then at 70° C. for a further 1 h and at 100° C. for a further 1 h. More Zn(CN)2, (147 mg, 1.252 mmol) Pd2(dba)3 (48 mg, 0.052 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (58 mg, 0.104 mmol) was then added and the reaction was heated at 100° C. for a further 1 h. The reaction was then cooled and treated with water (200 ml). The reaction was then extracted with DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using an ethyl acetate/hexane gradient to provide the desired compound (374 mg, 85%).

Workup

  1. waitat 100° C. for a further 1 h
  2. temperaturethe reaction was heated at 100° C. for a further 1 h
  3. temperatureThe reaction was then cooled
  4. extractionThe reaction was then extracted with DCM (3×200 ml)
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customthe crude residue purified by chromatography on silica gel using an ethyl acetate/hexane gradient

Sources & evidence

ORD record
ord-3c40e22b6c18445180b31374c81792d3
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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