Potassium Carbonate → HCID 66612102, compound

HRID 1019999Notes

Reaction equation

HRID 1019999 reaction equation
FC(F)(F)C([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:16]([O-:18])=[O:17])=[CH:10][C:11]=2I)[CH2:6]1)=O.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl.CO>CCOCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].ClCCl.O.O.C(#N)C>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:11]1[CH:10]=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=[C:7]2[C:12]=1[CH2:13][CH2:14][NH:5][CH2:6]2

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 21893726Hydrochloride methanolHCID 21956801HCID 21956801, compound

Product 1

HCID 66612102HCID 66612102, compound

Reagents, catalysts & solvents 5

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

2,2,2-Trifluoro-1-(5-iodo-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)ethanone (0.8 g, 2 mmoles) and 2-chlorophenyl boronic acid (0.31 g, 2 mmoles) were stirred with an acetonitrile water mixture (50:50, 28 mls). Anhydrous potassium carbonate (0.55 g, 4 mmoles) was then added under a stream of nitrogen. To this solution was then added palladium tetra(triphenyl phosphine) (tetrakis, 0.12 g, catalytic) and the solution heated (95° C.) for three hours. The reaction mixture was cooled to room temperature and water (10 mls) added followed by dichloromethane (3×60 mls), the combined dichloromethane extracts were washed with brine (20 mls) and dried over magnesium sulphate. The solution was then filtered and evaporated to leave an orange gum which was then dissolved in ether (20 mls) to which was added HCl/MeOH (4M) dropwise to afford a beige precipitate which was collected and dried (0.62 g, 95%, 90% pure).

Workup

  1. washthe combined dichloromethane extracts were washed with brine (20 mls)
  2. dry with materialdried over magnesium sulphate
  3. filtrationThe solution was then filtered
  4. customevaporated
  5. customto leave an orange gum which
  6. customto afford a beige precipitate which
  7. customwas collected
  8. customdried (0.62 g, 95%, 90% pure)

Sources & evidence

ORD record
ord-7b5f92ad2fd241eea43bc82011e7059c
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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