Dimethylformamide → HCID 86729569, compound

HRID 2175408Notes

Reaction equation

HRID 2175408 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][CH2:10][C:11]2[S:12][C:13]([CH3:16])=[N:14][N:15]=2)[C:3]=1I.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].[CH3:29][N:30](C=O)C>[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]>[NH2:8][C:6]1[N:7]=[C:2]([Cl:1])[C:3]([C:29]#[N:30])=[C:4]([NH:9][CH2:10][C:11]2[S:12][C:13]([CH3:16])=[N:14][N:15]=2)[N:5]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86729570HCID 86729570, compound

Product 1

HCID 86729569HCID 86729569, compoundYield 43%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 16-2 (639 mg, 1.67 mmol), and zinc cyanide (98 mg, 0.84 mmol) in DMF (6 mL) under nitrogen was added Pd2(dba)3 (76 mg, 0.08 mmol) and DPPF (93 mg, 0.17 mmol) and the resulting mixture was heated to 120° C. for 90 minutes. The reaction was allowed to cool and partititioned between ethyl acetate and a saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 10-100% ethyl acetate/hexane gradient gave 16-3 as a solid (200 mg, 43%). MS (ES) (M+H)+: observed=282.2, calculated=282.7.

Workup

  1. temperatureto cool
  2. concentrationThe organic phase was concentrated
  3. customflash column separation

Sources & evidence

ORD record
ord-a5bd663b78da42649a690639de846aa6
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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