Dimethylacetamide → HCID 89648092, compound

HRID 1773944Notes

Reaction equation

HRID 1773944 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([OH:22])[CH:15]=[CH:16][C:17]=2Br)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[C:24]([N:26](C)C)=O>CCOC(C)=O.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([OH:22])[CH:15]=[CH:16][C:17]=2[C:24]#[N:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 2

HCID 31374DimethylacetamideHCID 89648980HCID 89648980, compound

Product 1

HCID 89648092HCID 89648092, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-bromo-8-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (123 mg, 0.31 mmol, 1.0 eq.) in DMAC (0.62 mL), zinc cyanide (18 mg, 0.16 mmol, 0.5 eq.), tris(dibenzylideneacetone)dipalladium(0) (6.2 mg, 7 μmol, 0.02 eq.), 1,1′-bis-(diphenylphosphino)-ferrocene (4.7 mg, 8 μmol, 0.03 eq.) and poly(methylhydrosiloxane) (6 μL) were added. The resulting mixture was stirred at 150° C. under microwave irradiation for 30 min. The reaction mixture was diluted with AcOEt and water was added. The layers were separated and the org. layer was dried over MgSO4, filtered over celite, and concentrated in vacuo. The residue was purified by flashmaster (column: 10 g, flow: 15 mL/min, 25 fractions of 15 mL, Heptane+5% AcOEt to Heptane+40% AcOEt) to yield the title compound as a beige solid.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. dry with materiallayer was dried over MgSO4
  4. filtrationfiltered over celite
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flashmaster (column: 10 g, flow: 15 mL/min, 25 fractions of 15 mL, Heptane+5% AcOEt to Heptane+40% AcOEt)

Sources & evidence

ORD record
ord-fcf1ab34bacc46e7ac4256aab8a3c8d5
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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