Sodium Carbonate → HCID 86630687, compound

HRID 1851210Notes

Reaction equation

HRID 1851210 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[C:15]([CH2:17][CH3:18])[N:16]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:17]([C:15]1[N:16]=[C:4]2[N:3]=[C:2]([C:24]3[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[N:14]=1)[CH3:18]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86630685HCID 86630685, compound

Product 1

HCID 86630687HCID 86630687, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 3.90 g of the crude product obtained in step 3 and 3.00 g 4-formylphenylboronic acid in 180 mL 1,2-dimethoxyethane were added 0.55 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and 25 mL of a 10% w/w sodium carbonate solution. The resulting mixture was heated to 90° C. under an inert gas atmosphere for 20 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate, the solvent was evaporated and the residue was suspended in ethyl acetate. The crude product was isolated by filtration, which was purified on silica gel (dichloromethane/methanol).

Workup

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e71e00d7aefa492e959dc257953ff0ff
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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