2-Bromopyridine → 2-Fluoro-3-(pyridin-2-yl)benzaldehyde

HRID 594218Notes

Reaction equation

HRID 594218 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[C:14]([CH:15]=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[F:8][C:9]1[C:10]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:11][CH:12]=[CH:13][C:14]=1[CH:15]=[O:16]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 162178292-Fluoro-3-formylphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 866956082-Fluoro-3-(pyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of commercially available 2-bromopyridine (200 mg; 1.26 mmol), (2-fluoro-3-formylphenyl)boronic acid (212 mg; 1.26 mmol), K2CO3 (699 mg; 5.06 mmol), and PdCl2(dbpf) (11 mg; 0.017 mmol) in MeCN (5 ml) and water (5 ml) was heated to 80° C., under nitrogen, for 2 h. After cooling to rt, MeCN was removed under reduced pressure, and the aq. layer was extracted with AcOEt (2×). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (toluene/AcOEt=8/2) afforded 2-fluoro-3-(pyridin-2-yl)benzaldehyde as a yellow solid. LC-MS (conditions C): tR=0.78 min.; [M+H]+: 202.20 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. customMeCN was removed under reduced pressure
  3. extractionthe aq. layer was extracted with AcOEt (2×)
  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 (toluene/AcOEt=8/2)

Sources & evidence

ORD record
ord-19c7bf43e61146b3a1f054535707121d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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