Potassium Carbonate → HCID 57950436, compound

HRID 930774Notes

Reaction equation

HRID 930774 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.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>[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-4methoxyphenylboronic 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-13bf05fa388f43b5b5123486fe6ae577
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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