Dimethylformamide → HCID 68602934, compound

HRID 2090214Notes

Reaction equation

HRID 2090214 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[N:15][C:16]=3[O:18][CH2:19][CH3:20])[NH:11][C:10]([CH3:21])=[C:9]2[C:22]([O:24][CH2:25][CH2:26][C:27]#[N:28])=[O:23])=[C:4]([O:29][C:30]([F:33])([F:32])[F:31])[CH:3]=1.[CH3:34][N:35](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:34]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[N:15][C:16]=3[O:18][CH2:19][CH3:20])[NH:11][C:10]([CH3:21])=[C:9]2[C:22]([O:24][CH2:25][CH2:26][C:27]#[N:28])=[O:23])=[C:4]([O:29][C:30]([F:32])([F:33])[F:31])[CH:3]=1)#[N:35]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 68600565HCID 68600565, compound

Product 1

HCID 68602934HCID 68602934, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
220 °C

Procedure

4.59 g (8.72 mmol) of the compound from Example 35A, 758 mg (6.45 mmol) of zinc cyanide and 504 mg (0.436 mmol) of tetrakis(triphenylphosphine)palladium(0) are dissolved in 40 ml of DMF and then, divided into three mixtures, heated in a single mode microwave (Emrys Opzimizer) at 220° C. for 5 min. The individual mixtures are then recombined, and the solvent is removed in a rotary evaporator. The crude product is taken up in ethyl acetate and filtered through kieselguhr. The organic phase is washed with water (2×) and with saturated sodium chloride solution. After removal of the solvent by distillation, the crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 7:3→1:1). 1.40 g (31% of theory) of the title compound are obtained.

Workup

  1. customthe solvent is removed in a rotary evaporator
  2. filtrationfiltered through kieselguhr
  3. washThe organic phase is washed with water (2×) and with saturated sodium chloride solution
  4. customAfter removal of the solvent
  5. distillationby distillation
  6. customthe crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 7:3→1:1)

Sources & evidence

ORD record
ord-7391bcdd1a05492e832e4a791a9e5d38
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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