Cesium carbonate → HCID 86619576, compound

HRID 2236482Notes

Reaction equation

HRID 2236482 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].[CH:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)=[O:15].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>[CH:14]([C:16]1[CH:21]=[C:20]([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:19]=[CH:18][CH:17]=1)=[O:15]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343563-Formylphenylboronic acidHCID 42625597HCID 42625597, compound

Product 1

HCID 86619576HCID 86619576, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Iodo-3-methoxymethoxy-benzonitrile (600 mg, 2.08 mmol), 3-formylphenylboronic acid (450 mg, 3.0 mmol), Pd(PPh3)4 (200 mg, 0.17 mmol) and Cs2CO3 (1.2 g, 3.7 mmol) were mixed in N,N-dimethylformamide (15 mL), degassed and heated at 100° C. for 2 hours. After which, the mixture is allowed to cool to room temperature, an aqueous work up is performed, and the residue purified to afford the desired product (500 mg, 90%).

Workup

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

Sources & evidence

ORD record
ord-21bf8bab3ad14ab8b3c481047ebf681b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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