Dimethylformamide → HCID 178510690, compound

HRID 2203349Notes

Reaction equation

HRID 2203349 reaction equation
[CH3:1][N:2](C=O)C.I[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1>O.[C-]#N.[Zn+2].[C-]#N.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].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]>[NH:9]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]([C:1]#[N:2])=[N:8]1

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 178506575HCID 178506575, compound

Product 1

HCID 178510690HCID 178510690, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A DMF (180 mL) solution containing the intermediate from Step B above (24.1 g, 98 mmol), zinc cyanide (6.93 g, 59.0 mmol), 1,1′-bis(diphenylphosphino)ferrocene (4.36 g, 7.87 mmol) and tris(dibenzylideneacetone)dipalladium (3.60 g, 3.93 mmol) was heated at 120° C. for 1.5 hours. The solution was cooled to room temperature and diluted with water. The precipitated product was collected and dried under vacuum with a nitrogen sweep to give the title compound. 1H NMR (400 MHz, CH3CN-d3): δ 12.42 (s, 1H); 8.67 (dd, J=4.48, 1.53 Hz, 1H); 8.29 (dd, J=8.22, 1.53 Hz, 1H); 7.40 (dd, J=8.23, 4.48 Hz, 1H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe precipitated product was collected
  3. customdried under vacuum with a nitrogen sweep

Sources & evidence

ORD record
ord-3b59de4ab6154eb1a272082f7840d808
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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