Potassium Carbonate → HCID 67126306, compound

HRID 514140Notes

Reaction equation

HRID 514140 reaction equation
FC(F)(S(O[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([Br:27])=[CH:19][C:18]=1[C:28]#[N:29])(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.[Cl:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.[C:41]([O-])([O-])=O.[K+].[K+]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].CCO.C1(C)C=CC=CC=1>[Br:27][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([C:35]2[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=2)=[C:18]([C:28]#[N:29])[C:19]=1[CH3:41]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86691565HCID 86691565, compound

Product 1

HCID 67126306HCID 67126306, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a 50-50 (v/v) EtOH-toluene solution (4 mL) of 4-bromo-2-cyanonaphthalen-1-yl perfluorobutanesulfonate (3.99 g, 7.33 mmol) in a 2-5 mL microwave vial was added 4-chlorophenylboronic acid (1.65 g, 10.55 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (165 mg, 0.171 mmol) and 6 mL of 2 M K2CO3. The vial was sealed, and heated thermally at 60° C. for 30 minutes. The mixture was concentrated in vacuo, redissolved in EtOAc and washed with saturated NH4Cl and brine then dried with sodium sulfate and concentrated. The residue was chromatographed on silica gel using EtOAc and hexanes to give a mixture of products. This mixture was then purified by hot filtration using neat hexanes (50 mL) to give rise to desired pure product (731 mg, 28% yield). A second crop (600 mg) was obtained by repeating the hot filtration that was contaminated with starting material. 1H-NMR: (400 MHz, MeOH-d4): δ 8.361 (d, J=8.4 Hz, 1H); 7.89-7.85 (m, 1H); 7.69-7.62 (m, 3H); 7.56-7.49 (m, 3H); 2.81 (s, 3H).

Workup

  1. customThe vial was sealed
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionredissolved in EtOAc
  4. washwashed with saturated NH4Cl and brine
  5. dry with materialthen dried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. customto give
  9. additiona mixture of products
  10. filtrationThis mixture was then purified by hot filtration

Sources & evidence

ORD record
ord-4f29df5cd72b485c87286b8e37e3db6c
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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