Sodium Carbonate → HCID 68276348, compound

HRID 1487398Notes

Reaction equation

HRID 1487398 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N+:21]([C:10]1[CH:9]=[C:8]([C:27]2[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=2)[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O-:23])=[O:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 68276348HCID 68276348, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

1.67 g of bis(triphenylphosphine)palladium(II)chloride (2.38 mmol) and 15.8 g of sodium carbonate (149 mmol) are added to a solution of 18 g of tert-butyl 4-bromo-2-nitrobenzoate (59.6 mmol) and 10.98 g of pyridine-4-ylboronic acid (89 mmol) in a mixture of 200 ml of dimethoxyethane and 100 mL of water. The reaction medium is heated at 100° C. for 24 hours and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (CH2Cl2/AcOEt: 100:0 to 70:30, 30 min). The product is isolated in the form of an oil which crystallizes to yield 14.64 g (82%) of crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customis purified by flash chromatography (CH2Cl2/AcOEt: 100:0 to 70:30, 30 min)
  4. customThe product is isolated in the form of an oil which
  5. customcrystallizes

Sources & evidence

ORD record
ord-0514d6aad23742a39542bdcd2f99508c
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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