Dimethylformamide → HCID 69224107, compound

HRID 2223231Notes

Reaction equation

HRID 2223231 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.CCCCCC.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[CH3:39][N:40](C=O)C>[C-]#N.[C-]#N.[Zn+2].[Zn].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+:17]([C:14]1[CH:15]=[CH:16][C:11]([C:7]2[NH:8][C:9]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([C:39]#[N:40])[CH:10]=3)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 59715170HCID 59715170, compound

Product 1

HCID 69224107HCID 69224107, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To an oven dried 250 mL flask, 2.77 g of 2A (1 eq), 1.85 g Zn(CN)2 (1.8 eq), 68 mg of Zn powder and 160 mg (0.02 eq) of Pd2 dba3 were added followed by 75 mL of dry DMF. Under magnetic stirring, 1.07 mL of 10% hexane solution (0.04 eq) of PtBu3 was added and the mixture was stirred at room temperature for a period of 30 min followed by heating at 100° C. for another 35 min. The mixture was cooled to room temperature and poured into ice water. The solid was collected, washed with water and dried. The product was dissolved in THF, filtered and concentrated to dryness to produce crude 3 that was used without purification in the next step.

Workup

  1. customTo an oven dried 250 mL flask
  2. temperatureby heating at 100° C. for another 35 min
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solid was collected
  5. washwashed with water
  6. customdried
  7. dissolutionThe product was dissolved in THF
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customto produce crude 3 that
  11. customwas used without purification in the next step

Sources & evidence

ORD record
ord-55e94e3ea9cb4790980aa6dc2b438dba
Source dataset
uspto-grants-2008_05
Patent number
US07375118B2

Reaction notes

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