Potassium Carbonate → HCID 86664381, compound

HRID 1019997Notes

Reaction equation

HRID 1019997 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([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:4].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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][N:5]([C:3](=[O:4])[C:2]([F:20])([F:19])[F:1])[CH2:6]2

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 27343222-Chlorophenylboronic acid2×HCID 21956801HCID 21956801, compound

Product 1

HCID 86664381HCID 86664381, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

2,2,2-Trifluoro-1-(5-iodo-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone (1MK1, 750 mgs, 1.88 mmoles) was dissolved in toluene (25 mls) and 2-chlorophenyl boronic acid (352 mg, 2.25 mmoles), anhydrous potassium carbonate (311 mg, 2.25 mmoles) and finally palladium tetrakis catalyst (111 mg, 0.099 mmoles, 5 mol %) was added. The reaction mixture was flushed with nitrogen and heated to 95° C. overnight. Starting material was still present therefore further 2-chlorophenyl boronic acid (88 mg, 0.56 mmoles), potassium carbonate (78 mg, 0.56 mmoles) and catalyst (28 mg, 0.025 mmoles) were added and the reaction continued for a further 2 hours. The reaction was then cooled and filtered through a pad of Celite. The filtrate was washed with saturated sodium bicarbonate solution (25 mls), water (25 mls) and brine (25 mls). The organic layer was dried over anhydrous magnesium sulphate, filtered and evaporated to give an oily residue. The oil was triturated with ether followed by isopropanol:hexane 1:1. The dark yellow solid (724 mg, 100% yield) was used without further purification. LC-MS (retention, 4.2 mins M+H 386).

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. temperatureThe reaction was then cooled
  3. filtrationfiltered through a pad of Celite
  4. washThe filtrate was washed with saturated sodium bicarbonate solution (25 mls), water (25 mls) and brine (25 mls)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oily residue
  9. customThe oil was triturated with ether

Sources & evidence

ORD record
ord-2c93b970e079476b8f3b2e5cc76a54e4
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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