Cesium carbonate → HCID 86729360, compound

HRID 521195Notes

Reaction equation

HRID 521195 reaction equation
[Cl-].[C:2]([CH:4]=[C:5]1[CH2:10][CH2:9][NH2+:8][CH2:7][CH2:6]1)#[N:3].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[C:48]([O:54][CH3:55])[CH:47]=1.C([O-])([O-])=O.[Cs+].[Cs+].[N-]=C=O>CC(O)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:53][O:52][C:49]1[CH:50]=[C:51]([N:8]2[CH2:9][CH2:10][C:5](=[CH:4][C:2]#[N:3])[CH2:6][CH2:7]2)[CH:46]=[CH:47][C:48]=1[O:54][CH3:55]

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 105034IsocyanateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86729359HCID 86729359, compound

Product 1

HCID 86729360HCID 86729360, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

In a sealed tube, 4-(cyanomethylidene)piperidinium chloride (16 mg, 0.10 mmol), Pd2(dba)3 (14 mg, 0.015 mmol), X-Phos (20 mg, 0.020 mmol), 4-bromo-1,2-dimethoxybenzene (33 mg, 0.15 mmol), and Cs2CO3 (98 mg, 0.30 mmol) were suspended in t-BuOH (0.5 mL). The reaction mixture was purged with argon for 5 minutes, the reaction flask was capped, and heated to 90° C. for 12 hours. The reaction was then cooled to ambient temperature and diluted with DMF:MeCN (1.0 mL, 50:50). To this mixture, Silica Supported-DMT (0.50 mmol, 0.57 mmol/g) followed by Silica Supported-Isocyanate (0.15 mmol, 1.33 mmol/g) was added. The resulting mixture was then shaken at 50° C. for 4 hours. The mixture was then passed through a nylon syringe filter (0.45 μm), and the filtrate was concentrated in vacuo to afford the title compound. The crude residue was used without further purification.

Workup

  1. customThe reaction mixture was purged with argon for 5 minutes
  2. customthe reaction flask was capped
  3. temperatureThe reaction was then cooled to ambient temperature
  4. additiondiluted with DMF
  5. customThe mixture was then passed through a nylon syringe
  6. filtrationfilter (0.45 μm)
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ff7b133c6a274b8b9bb03d1d3b1aeeb0
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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