Water → HCID 67055612, compound

HRID 38484Notes

Reaction equation

HRID 38484 reaction equation
O.Br[C:3]1[C:12]([O:13][CH2:14][CH3:15])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:16][CH2:17][CH3:18].[C:19]([O:23][C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[N:30][CH:31]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.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]([O:16][C:4]1[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[C:12]([O:13][CH2:14][CH3:15])[C:3]=1[C:28]1[CH:29]=[N:30][CH:31]=[C:26]([CH:27]=1)[C:24]([O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:25])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 57930905Methyl 4-bromo-3,5-diethoxybenzoateHCID 58208715[5-(tert-Butoxycarbonyl)pyridin-3-yl]boronic acid

Product 1

HCID 67055612HCID 67055612, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

H2O (59.4 mg, 3.30 mmol) was added to a stirred suspension of PdCl2(dppf) (12.1 mg, 0.0330 mmol), methyl 4-bromo-3,5-diethoxybenzoate (200 mg, 0.660 mmol), [5-(tert-butoxycarbonyl)pyridin-3-yl]boronic acid (177 mg, 0.792 mmol) and K3PO4 (420 mg, 1.98 mmol) in DME (4 ml) and the mixture was stirred at 90° C. overnight. The reaction mixture was filtered through celite pad, the filtrate was concentrated under reduced pressure. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compounds as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite pad
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silicagel column chromatography (hexane/EtOAc)
  4. customto give

Sources & evidence

ORD record
ord-49de55c05d7840eba97ada2ce82f42a6
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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