Water → HCID 68250502, compound

HRID 2383064Notes

Reaction equation

HRID 2383064 reaction equation
[C:1]1([C@H:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9][N:8]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.O.[CH3:54][N:55](C)C(=O)C>[Zn].[C-]#N.[Zn+2].[C-]#N.[Pd+2]>[C:54]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:1]=1[C@H:7]([C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[N:8]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:9][CH2:10]2)#[N:55]

Participants

8

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 86643135HCID 86643135, compound

Product 1

HCID 68250502HCID 68250502, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)Catalyst

Conditions

Temperature
95 °C

Procedure

Tert-butyl (1S)-1-phenyl-8-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydroisoquinoline-2(1H)-carboxylate (3.75 g) was dissolved in N,N-dimethylacetamide (40 mL). To the reaction mixture were added zinc (537 mg), zinc cyanide (1.15 g), trifluoroacetic palladium (II) (682 mg), and biphenyl-2-yl(di-tert-butyl)phosphine (1.22 g). The temperature was increased from room temperature to 95° C. over 45 minutes and then the mixture was stirred at 95° C. for 18 hours. Water was added to the mixture which was then filtered through celite. Thereafter, the mixture was extracted with diethyl ether. The extract was washed with a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (EtOAc:hexane) to obtain tert-butyl (1S)-8-cyano-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (796 mg).

Workup

  1. temperatureThe temperature was increased from room temperature to 95° C. over 45 minutes
  2. filtrationwas then filtered through celite
  3. extractionThereafter, the mixture was extracted with diethyl ether
  4. washThe extract was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (EtOAc:hexane)

Sources & evidence

ORD record
ord-02bd3fb2443a44329eb9e384814ab3cd
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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