Cesium carbonate → HCID 42625598, compound

HRID 2236477Notes

Reaction equation

HRID 2236477 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH2:11][O:12][CH3:13].[O:14]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.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>[O:14]1[CH:18]=[CH:17][C:16]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[O:10][CH2:11][O:12][CH3:13])=[CH:15]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 42625597HCID 42625597, compound

Product 1

HCID 42625598HCID 42625598, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Iodo-3-methoxymethoxy-benzonitrile (150 mg, 0.52 mmol) and 3-furanboronic acid (96 mg, 0.86 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol) and Cs2CO3 (500 mg, 1.53 mmol) is mixed in N,N-dimethylformamide (10 mL) and degassed and then heated at 100° C. for 4 hours. After which, the mixture is allowed to cool to room temperature and an aqueous work up is performed and the residue purified to afford the desired product (100 mg, 84%).

Workup

  1. customdegassed
  2. temperatureto cool to room temperature
  3. customthe residue purified

Sources & evidence

ORD record
ord-b1d3f9b91b514b80a030643536079b9b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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