HCID 86698150, compound → HCID 67991829, compound

HRID 1424493Notes

Reaction equation

HRID 1424493 reaction equation
Cl[C:2]1[C:7]2[N:8]([CH2:15][C:16]3[N:24]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]4=[N:20][CH:21]=[CH:22][CH:23]=[C:18]4[N:17]=3)[C:9](=[O:14])[N:10]([CH:11]([CH3:13])[CH3:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:30]([Zn]C#N)#[N:31]>CN(C=O)C>[CH2:25]([N:24]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[N:17]=[C:16]1[CH2:15][N:8]1[C:7]2[C:2]([C:30]#[N:31])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]([CH:11]([CH3:13])[CH3:12])[C:9]1=[O:14])[CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 86698150HCID 86698150, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 67991829HCID 67991829, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of compound 25 (0.075 g, 0.182 mmol), tetrakis(triphenyl-phosphine)palladium (41 mg, 0.036 mmol) and dicyanozinc (0.042 g, 0.363 mmol) in DMF (3 mL) under nitrogen atmosphere was irradiated for 30 minutes in a microwave reactor at 170° C. The resulting mixture was allowed to cool down to room temperature then filtered through an acrodisk filter and evaporated to dryness. The residue was purified by column chromatography using EtOAc. The title compound 29 was isolated as a white solid (60 mg, 81%).

Workup

  1. customwas irradiated for 30 minutes in a microwave reactor at 170° C
  2. filtrationthen filtered through an acrodisk
  3. filtrationfilter
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ade651abcf5c439990a54180ece8dd78
Source dataset
uspto-grants-2015_01
Patent number
US08927720B2

Reaction notes

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