Dimethylacetamide → HCID 68809138, compound

HRID 2219076Notes

Reaction equation

HRID 2219076 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C[C:22]([N:24](C)C)=O>[C-]#N.[Zn+2].[C-]#N.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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[Zn]>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:3][C:2]([C:22]#[N:24])=[CH:7][N:6]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 59771326HCID 59771326, compound

Product 1

HCID 68809138HCID 68809138, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 5-Chloro-2-(4-methylphenyl)-3-phenylpyridine (0.320 g, 1.144 mmol), zinc cyanide (0.081 g, 0.687 mmol), Pd2(dba)3 (0.063 g, 0.069 mmol), dppf (0.076 g, 0.137 mmol) and zinc (0.018 g, 0.275 mmol) in DMA (5 mL) was degassed (3×pump/N2) and heated to 150° C. for 20 hr. The reaction was then cooled to rt, concentrated, partitioned between EtOAc and water, and extracted 3× with EtOAc. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. Purfied by silica gel chromatography (0-20% EtOAc in Hexanes) to give the titled compound. 1H-NMR (500 MHz, CDCl3) δ 8.92 (d, 1H, J=2.0 Hz), 7.95 (d, 1H, J=2.2 Hz), 7.34-7.33 (m, 3H), 7.28-7.26 (1,2H), 7.20-7.18 (m, 2H), 7.07 (d, 2H, J=8.1 Hz), 2.33 (s, 3H) LRMS m/z (M+H) Calcd: 271.0, found: 271.0.

Workup

  1. customwas degassed (3×pump/N2)
  2. temperatureThe reaction was then cooled to rt
  3. concentrationconcentrated
  4. custompartitioned between EtOAc and water
  5. extractionextracted 3× with EtOAc
  6. dry with materialThe combined organics were dried (anhd. Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c8be4e77ad54e6da700463dd60719d0
Source dataset
uspto-grants-2008_08
Patent number
US07414055B2

Reaction notes

Loading…