Dimethylformamide → HCID 68183975, compound

HRID 879001Notes

Reaction equation

HRID 879001 reaction equation
Cl[C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=2)[C:7]([CH3:18])=[N:6]1.C1(P(C2CCCCC2)C2(C(C)C)CC(C(C)C)=CC(C(C)C)=C2C2C=CC=CC=2)CCCCC1.[CH3:58][N:59](C)C=O>[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]>[Cl:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([C:58]#[N:59])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=2)[C:7]([CH3:18])=[N:6]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 60152151HCID 60152151, compoundHCID 672859322-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl

Product 1

HCID 68183975HCID 68183975, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To a solution of the compound [97](30.1 mg) in N,N-dimethylformamide (0.9 mL) were added zinc cyanide (20.2 mg), tris(dibenzylideneacetone)dipalladium(0) (7.9 mg) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (5.1 mg) at room temperature, and then the reaction mixture was subjected to microwave irradiation at 150° C. for 2 hours. The reaction mixture was extracted with ethyl acetate, and then the obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by reverse phase preparative liquid chromatography to give the titled compound (5.0 mg) as a yellow solid.

Workup

  1. customirradiation at 150° C. for 2 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-030c7f65f93a42c2afbc30f268339644
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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