3-Bromopyridine → HCID 63893930, compound

HRID 879410Notes

Reaction equation

HRID 879410 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:22])=[C:18]([CH:21]=1)[CH:19]=[O:20]>C1COCC1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:22])=[C:18]([CH:19]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:20])[CH:21]=1

Participants

5

Reactant 3

HCID 122863-BromopyridineHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 63893930HCID 63893930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an oven-dried flask was added anhydrous THF (20 mL) and 3-bromopyridine (2 mL, 20 mmol). Isopropylmagnesium chloride in THF (11 mL, 2.0 M solution) was then added dropwise over several minutes. The mixture was stirred at room temperature for 1 hour, and then 5-bromo-2-fluorobenzaldehyde (2.4 mL, 20 mmol) was added. After stirring for 1 further hour at room temperature, the reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc, dried over MgSO4, and purified by column chromatography (gradient 0 to 50% EtOAc in hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.51 (d, J=1.9 Hz, 1H), 8.41 (dd, J=4.8, 1.5 Hz, 1H), 7.78-7.68 (m, 2H), 7.38 (ddd, J=8.7, 4.6, 2.6 Hz, 1H), 7.27 (dd, J=8.6, 4.2 Hz, 1H), 6.95-6.85 (m, 1H), 6.10 (s, 1H), 4.22 (br s, 1H).

Workup

  1. stirringAfter stirring for 1 further hour at room temperature
  2. customthe reaction was quenched with saturated aqueous NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. custompurified by column chromatography (gradient 0 to 50% EtOAc in hexanes)
  6. customto afford the product

Sources & evidence

ORD record
ord-4a707979cb9547e48d4bc8a6349f3364
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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