Dimethylacetamide → HCID 11266792, compound

HRID 1241708Notes

Reaction equation

HRID 1241708 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]([CH3:23])[C:15]4[C:10]=3[C:11]([CH:12]=[CH:13][CH:14]=4)=[C:4]2[CH:3]=1.C[C:25]([N:27](C)C)=O>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([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].[C-]#N.[Zn+2].[C-]#N>[CH3:23][N:16]1[C:15]2[C:10]3[C:11](=[C:4]4[C:5](=[N:8][C:9]=3[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]1=3)[CH:6]=[CH:7][C:2]([C:25]#[N:27])=[CH:3]4)[CH:12]=[CH:13][CH:14]=2

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 10925151HCID 10925151, compound2×

Product 1

HCID 11266792HCID 11266792, compoundYield 99%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

(Method T) 3-Chloro-8-methyl-8H-quino[4,3,2-kl]acridine, 28 (150 mg, 0.47 mmol), tris(dibenzylideneacetone)dipalladium (0) (9 mg), bisdiphenylphosphino ferrocene (17 mg), zinc powder (5 mg), zinc cyanide (33 mg) and DMA were mixed in a sealed tube, flushed with nitrogen, the tube sealed and the mixture heated to 100° C. for 3 days. The cooled mixture was taken up in dichloromethane (50 mL), washed with 2M ammonium hydroxide (20 mL) and water (20 mL), dried, filtered, evaporated and purified by column chromatography to the title compound (147 mg, 0.46 mmol, 99%).

Workup

  1. customflushed with nitrogen
  2. customthe tube sealed
  3. washwashed with 2M ammonium hydroxide (20 mL) and water (20 mL)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-beb9567c109d4541ace006cf3c7a2537
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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