Water → 2-Phenylpyridine-4-carbaldehyde

HRID 594214Notes

Reaction equation

HRID 594214 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[CH:5]=[O:6].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>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.CCOC(C)=O>[C:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=2)[CH:5]=[O:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27629912-Bromo-4-pyridinecarboxaldehyde

Product 1

HCID 463151012-Phenylpyridine-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of commercially available 2-bromoisonicotinaldehyde (3.000 g; 16.12 mmol), phenylboronic acid (3.009 g; 24.19 mmol), and Pd(PPh3)4 (931 mg; 0.80 mmol) in toluene (40 ml) and aq. 2 M Na2CO3 (34 ml) was heated to reflux, under nitrogen, for 4 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded 2-phenylisonicotinaldehyde as a yellow oil. LC-MS (conditions A): tR=0.39 min.; [M+H]+: 184.47 g/mol.

Workup

  1. temperaturewas heated
  2. temperatureto reflux, under nitrogen, for 4 h
  3. extractionThe separated aq. layer was further extracted with AcOEt
  4. washThe mixed organic layers were washed with brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (heptane/AcOEt=7/3)

Sources & evidence

ORD record
ord-0b037a0f36c4450dbbaf8f4b53e6aee4
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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