Dimethylformamide → 6-Chloro-5-fluoropyridine-3-carbaldehyde

HRID 2066862

반응식

HRID 2066862 반응식
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([F:14])[C:10]([Cl:13])=[N:11][CH:12]=1.CN([CH:18]=[O:19])C.CCOC(C)=O>CCOCC>[Cl:13][C:10]1[N:11]=[CH:12][C:7]([CH:18]=[O:19])=[CH:8][C:9]=1[F:14]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 27632855-Bromo-2-chloro-3-fluoropyridineHCID 178418339Butyllithium

생성물 1

HCID 216981946-Chloro-5-fluoropyridine-3-carbaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Butyl lithium (2.5 M in hexane, 2.5 mL, 6.3 mmol) was added to 5-bromo-2-chloro-3-fluoro-pyridine (1 g, 4.75 mmol) in 10 mL of ether at −78° C. After 10 minutes, DMF (5 mL) was added and the mixture was warmed to room temperature over 1 h. The mixture was poured into 20 mL of EtOAc and the mixture was washed with water (20 mL) and brine (20 mL), dried over magnesium sulfate and concentrated to afford the crude 53a (0.92 g) as a brown oil: LC-MS160.0 (MH+).

후처리

  1. washthe mixture was washed with water (20 mL) and brine (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c4d725c0dae449cf9394add94b98aae3
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293729B2

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