Cesium carbonate → HCID 59299836, compound

HRID 2236488Notes

Reaction equation

HRID 2236488 reaction equation
Br[C:2]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:14])[CH:3]=1.[O:15]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16]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>[F:14][C:4]1[CH:3]=[C:2]([C:17]2[CH:18]=[CH:19][O:15][CH:16]=2)[C:9]([O:10][CH2:11][O:12][CH3:13])=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 593002954-Bromo-2-fluoro-5-(methoxymethoxy)benzaldehyde

Product 1

HCID 59299836HCID 59299836, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-2-fluoro-5-methoxymethoxy-benzaldehyde (160 mg, 0.61 mmol) and 3-furanboronic acid (100 mg, 0.90 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol) and Cs2CO3 (400 mg, 1.23 mmol) were mixed in N,N-dimethylformamide (10 mL) and degassed and then heated at 100° C. for 1 hour. The mixture is allowed to cool to room temperature and an aqueous work up is performed. The residue is purified to afford the desired product (60 mg, 39%).

Workup

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

Sources & evidence

ORD record
ord-576b27cc0ba54b7ebe6a1453754d4778
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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