Cesium carbonate → HCID 86729360, compound

HRID 1852462Notes

Reaction equation

HRID 1852462 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. LRMS (ESI) calc'd for C15H15N2O2 [M+H]+: 259. Found: 259.

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/MeCN (1.0 mL, 50:50)
  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-5e32ec9c743a4a898f6dee69c9a4a2c8
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

Loading…