Toluene → 5-(3-Fluorophenyl)pyridine-2-carbaldehyde

HRID 1630405Notes

Reaction equation

HRID 1630405 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[F:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1>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.C(O)C.O>[F:10][C:11]1[CH:16]=[C:15]([C:2]2[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 463131125-(3-Fluorophenyl)pyridine-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2 g of 5-bromopyridine-2-carbaldehyde, 1.96 g of 3-fluorophenylboronic acid, 11.2 g of K2CO3, 160 ml of toluene, 60 ml of water, 60 ml of ethanol and 0.93 mg of tetrakis(triphenylphosphine)palladium (0) is stirred at 100° C. under argon for 2 hours. The solvents are evaporated and the residue is dispersed in 100 ml of water, and the product is extracted with 2 portions of 30 ml of ethyl acetate. The organic phase is washed with 30 ml of sat. brine, dried over sodium sulfate and concentrated. The resulting residue is recrystallized from 28 ml of isopropanol.

Workup

  1. customThe solvents are evaporated
  2. additionthe residue is dispersed in 100 ml of water
  3. extractionthe product is extracted with 2 portions of 30 ml of ethyl acetate
  4. washThe organic phase is washed with 30 ml of sat. brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is recrystallized from 28 ml of isopropanol

Sources & evidence

ORD record
ord-419c36b3ccb74bce93aee6fa046a0ea0
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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