Dimethylformamide → HCID 68523117, compound

HRID 1515226Notes

Reaction equation

HRID 1515226 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[O:6][CH2:7][C:8]3[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=3[C:10](=[C:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[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].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]>[CH3:17][N:14]1[CH2:13][CH2:12][C:11](=[C:10]2[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][O:6][C:5]3[CH:22]=[CH:23][C:2]([C:24]#[N:25])=[CH:3][C:4]2=3)[CH2:16][CH2:15]1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 24898775HCID 24898775, compound

Product 1

HCID 68523117HCID 68523117, compoundYield 72%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Zn(CN)2 (4.70 g, 40.0 mmol), Pd2(dba)3 (0.23 g, 0.25 mmol), and DPPF (0.30 g, 0.50 mmol) were added to a DMF (100 mL) solution of 4-(2-bromo-6H-dibenz[b,e]oxepin-11-ylidene)-1-methylpiperidine (14.8 g, 40.0 mmol) in an argon atmosphere, and the mixture was stirred overnight at 80° C. Insoluble matters were filtered off, a saturated sodium chloride solution (50 mL) was then added to the filtrate, and the product was extracted with ethyl acetate. The solvent was distilled off under a reduced pressure, and thereafter the residue was purified by silica gel column chromatography (chloroform-methanol=9:1), to give 9.14 g (72%) of the captioned compound in the form of crystals.

Workup

  1. filtrationInsoluble matters were filtered off
  2. additiona saturated sodium chloride solution (50 mL) was then added to the filtrate
  3. extractionthe product was extracted with ethyl acetate
  4. distillationThe solvent was distilled off under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform-methanol=9:1)

Sources & evidence

ORD record
ord-a4d175bdcbe5401a9ec8daf0587902cd
Source dataset
uspto-grants-2012_07
Patent number
US08222419B2

Reaction notes

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