Water → HCID 58307191, compound

HRID 448448Notes

Reaction equation

HRID 448448 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4]N=1.[CH2:11]([O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:12].[C:25]([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:2]=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2389326-Bromonicotinic acidHCID 46738762(3-Ethoxy-4-methoxyphenyl)boronic acid

Product 1

HCID 58307191HCID 58307191, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

6-Bromonicotinic acid (2.02 g, 10.0 mmol) was dissolved in DME (80 mL) under nitrogen. Pd(PPh3)4 (0.58 g, 0.5 mmol) was added, and the resulting mixture was stirred at ambient temperature for 15 minutes. 3-ethoxy-4-methoxyphenylboronic acid (2.4 g, 12.2 mmol) and 2N Na2CO3 (40 mL, 80 mmol) were added, and the resulting mixture was heated to reflux with stirring for 24 hours. The mixture was poured into 300 mL of water and extracted with ethyl acetate (3×200 mL), and the product precipitated upon standing, providing 2.05 g of the product in 76% yield: 1H NMR (CDCl3) δ 1.53 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.22 (q, J=7.0 Hz, 2H), 7.00 (d, J=8.6 Hz, 1H), 7.53-7.58 (m, 2H), 7.91-8.02 (m, 2H), 8.12 (dd, J=6.9 Hz, J=1.5 Hz, 1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. stirringwith stirring for 24 hours
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. customthe product precipitated

Sources & evidence

ORD record
ord-b775f6c250fb4a8d8703bc841047ada8
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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