Methanol → HCID 68518415, compound

HRID 639927Notes

Reaction equation

HRID 639927 reaction equation
FC(F)(F)S(O[CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[C:9]([C:25]#[N:26])[NH:8]1)(=O)=O.CN([CH:32]=[O:33])C.[OH2:34].C(N(CC)CC)C.[CH3:42]O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:25]([C:9]1[N:8]=[C:7]([C:42]([O:33][CH3:32])=[O:34])[C:16]2[C:11]([C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)#[N:26]

Participants

8

Reactant 5

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 86609505HCID 86609505, compound

Product 1

HCID 68518415HCID 68518415, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
70 °C

Procedure

3-cyano-6-methoxy-4-pyridin-2-yl-1,2-dihydroisoquinolin-1-yl trifluoromethanesulfonate (0.267 g, 0.652 mmol), DMF (3.5 mL), MeOH (1.75 mL) and H2O (0.012 mL, 0.652 mmol) were combined in a r.b. flask and bubbled CO through this mixture for 3 min. Triethylamine (0.132 g, 1.305 mmol), dppf (0.072 g, 0.13 mmol) and Pd(OAc)2 (0.015 g, 0.065 mmol) were added to the above mixture and CO was bubbled for 1 min. Stirred under atmospheric CO at 70° C. for 2 h. Cooled to rt. Partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×). Combined organic layers were dried over Na2SO4 and concentrated. Purified by flash chromatography: 5% to 70% EA in hexanes. Tan solid (0.067 g, 32%).

Workup

  1. customflask and bubbled CO through this mixture for 3 min
  2. customwas bubbled for 1 min
  3. temperatureCooled to rt
  4. customPartitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialCombined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customPurified by flash chromatography

Sources & evidence

ORD record
ord-360db077ab5a4ccc879b6bf84a128c51
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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