Benzaldehyde → HCID 90013746, compound

HRID 589009Notes

Reaction equation

HRID 589009 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1.[CH:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[Br:13][C:14]1[C:19]([CH2:20][CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:28])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 7912DiisopropylamineHCID 2208322-Bromo-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 90013746HCID 90013746, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
5 °C

Procedure

A solution of n-butyllithium in hexanes (2.5 M, 27.9 mL, 0.0698 mol) was added dropwise over a period of 30 min to a solution of N,N-diisopropylamine (9.9 mL, 0.069 mol, 1.2 equiv) in anhydrous THF (40 mL) at −78° C. The resulting mixture was slowly warmed to 5° C. over 30 min, then cooled to −78° C., and a solution of 2-bromo-3-methylpyridine (6.5 mL, 0.058 mol) in anhydrous THF (20 mL) was added dropwise over 45 min and stirred for 1 h. A solution of benzaldehyde (7.1 mL, 0.069 mol) in THF (20 mL) was then added dropwise over 15 min. The resulting solution was gradually warmed to 23° C. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in petroleum ether to give the title compound. MS: m/z=280.0 (M+1).

Workup

  1. temperaturecooled to −78° C.
  2. temperatureThe resulting solution was gradually warmed to 23° C
  3. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ff084750f9c943a088629550d18d501e
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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