Sodium Carbonate → HCID 68683880, compound

HRID 1295419Notes

Reaction equation

HRID 1295419 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].Br[C:8]1[CH:28]=[CH:27][C:11]([CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][NH:14]2)=[CH:10][CH:9]=1.[OH-].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].O.O.C(O)(=O)C(O)=O>CC([O-])=O.CC([O-])=O.[Pd+2].C(Cl)Cl>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][CH:13]3[C:22]4[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=4)[CH2:16][CH2:15][NH:14]3)=[CH:10][CH:9]=2)=[CH:34][CH:33]=1

Participants

9

Reactant 6

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 61373Oxalic acid dihydrateHCID 2856454-Fluorophenylboronic acidHCID 68685035HCID 68685035, compound

Product 1

HCID 68683880HCID 68683880, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(4′-Fluoro-biphenyl-4-ylmethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline oxalate (37) was prepared as follows: 1-(4-bromo-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline oxalate (0.452 g, 1 mmol) was added to a mixture of 20 mL CH2Cl2 and 20 ml of 1N NaOH. The reaction mixture was stirred at room temperature. After dissolving of precipitate organic phase was separated, dried over Na2SO4, filtered and evaporated. A residue was dissolved in 6 mL i-PrOH. 4-Fluoro-phenyl-boronic acid (0.153 g, 1.09 mmol) was added. The resulting solution was stirred for 30 min at room temperature. Pd(OAc)2 (1 mg, 0.0045 mmol), PPh3 (9 mg, 0.034 mmol) and 2N Na2CO3 (1 mL, 2 mmol) were added, the reaction mixture was refluxed for 6 h under Ar and evaporated. A residue was dissolved in chloroform and washed with 1N NaOH. Organic phase was dried under Na2SO4, filtered and evaporated. A residue was dissolved in MeOH, a solution of oxalic acid dihydrate (0.259 g, 2.05 mmol) was added under reflux. Oxalic acid salt was crystallized from MeOH—Et2O mixture. Yield is 0.294 g (62.9%).

Workup

  1. dissolutionAfter dissolving of precipitate organic phase
  2. customwas separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionA residue was dissolved in 6 mL i-PrOH
  7. stirringThe resulting solution was stirred for 30 min at room temperature
  8. temperaturethe reaction mixture was refluxed for 6 h under Ar
  9. customevaporated
  10. dissolutionA residue was dissolved in chloroform
  11. washwashed with 1N NaOH
  12. customOrganic phase was dried under Na2SO4
  13. filtrationfiltered
  14. customevaporated
  15. dissolutionA residue was dissolved in MeOH
  16. temperatureunder reflux
  17. customOxalic acid salt was crystallized from MeOH—Et2O mixture

Sources & evidence

ORD record
ord-0a8a5cffb80843eba6a5cbf2472f4eaa
Source dataset
uspto-grants-2007_07
Patent number
US07241774B2

Reaction notes

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