1,3-Bis(diphenylphosphino)propane → HCID 68869055, compound

HRID 1984852Notes

Reaction equation

HRID 1984852 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=2)=[O:4].[C:29]([O-:32])(=[O:31])C.[K+].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CS(C)=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]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:29]([OH:32])=[O:31])[CH:9]=2)=[O:4]

Participants

7

Reactant 3

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 517044Potassium AcetateHCID 86597134HCID 86597134, compound

Product 1

HCID 68869055HCID 68869055, compoundYield 33.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-cyclopentylmethyl-7-trifluoromethanesulfonyloxy-isoquinoline-3-carboxylic acid methyl ester (0.150 g, 0.359 mmol) in DMSO (7.0 mL) was added potassium acetate (0.317 g, 3.23 mmol), dppf(0.140 mmol), dppp (50 mg), and Pd(OAc)2 (20 mg). The reaction mixture was degassed under vacuum for 5 min and then CO gas was purged through the reaction mixture for 10 min. The reaction mixture was then heated at 75° C. overnight under an atmosphere of CO gas. The reaction mixture was diluted with DCM and extracted with 10% citric acid solution. The organic phase was dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel using EtOAc to give 38 mg of 1-cyclopentylmethyl-isoquinoline-3,7-dicarboxylic acid 3-methyl ester as a white solid.

Workup

  1. customThe reaction mixture was degassed under vacuum for 5 min
  2. customCO gas was purged through the reaction mixture for 10 min
  3. additionThe reaction mixture was diluted with DCM
  4. extractionextracted with 10% citric acid solution
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-c769d76a09844577b501cd8ea20808c0
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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