HCID 86698150, compound → HCID 67991829, compound

HRID 632862Notes

Reaction equation

HRID 632862 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-4cabfb005dad458a819035fb050177b0
Source dataset
uspto-grants-2016_04
Patent number
US09321767B2

Reaction notes

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