Potassium Carbonate → HCID 57950436, compound

HRID 1020691Notes

Reaction equation

HRID 1020691 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[F:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 140623094-Bromo-2-methoxypyridineHCID 15789384(2-Fluoro-4-methoxyphenyl)boronic acid

Product 1

HCID 57950436HCID 57950436, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromo-2-methoxypyridine (1.39 g, 7.42 mmol), 2-fluoro-4-methoxyphenylboronic acid (2.40 g, 14.1 mmol), K2CO3 (2.05 g, 14.8 mmol) and bis(triphenylphosphine) palladium(II) chloride (Pd(PPh3)2Cl2) (52 mg, 0.74 mmol) were stirred in DMSO (8.5 mL) under vacuum for 20 min. The flask was flushed with argon and the mixture was heated to 90° C. for 3 h. Upon cooling, the mixture was diluted with brine, and the aqueous solution was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with water (3×20 mL), dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (40+M Biotage column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 80:20) provided the title compound (0.98 g, 57%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 8.20 (d, J=5.4 Hz, 1H), 7.42-7.38 (m, 1H), 7.07 (d, J=5.4 Hz, 1H), 6.93 (s, 1H), 6.80 (dd, J=8.6, 2.5 Hz, 1H), 6.74 (dd, J=12.6, 2.5 Hz, 1H), 3.99 (s, 3H), 3.85 (s, 3H).

Workup

  1. customThe flask was flushed with argon
  2. temperatureUpon cooling
  3. additionthe mixture was diluted with brine
  4. extractionthe aqueous solution was extracted with CH2Cl2 (3×50 mL)
  5. washThe combined organic extracts were washed with water (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d70322443414478e947badec03d6fe57
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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