2-Amino-5-fluoro-N-methoxy-N-methylbenzamide → 3-Methylpyridine-2-carboxaldehyde

HRID 1616071

반응식

HRID 1616071 반응식
NC1C=CC(F)=CC=1[C:4](N(OC)C)=[O:5].C([Mg]Cl)(C)C.[CH3:20][C:21]1[C:22]([Mg]Br)=[N:23][CH:24]=[CH:25][CH:26]=1>C1COCC1>[CH3:20][C:21]1[C:22]([CH:4]=[O:5])=[N:23][CH:24]=[CH:25][CH:26]=1

참가 물질

5

반응물 3

HCID 534075722-Amino-5-fluoro-N-methoxy-N-methylbenzamideHCID 178418918HCID 178418918, 화합물HCID 178426302HCID 178426302, 화합물

생성물 1

HCID 15018743-Methylpyridine-2-carboxaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-amino-5-fluoro-N-methoxy-N-methylbenzamide (1.0 g, 5.05 mmol) in THF (4.2 mL) was added isopropylmagnesium chloride (2.0M in THF, 5.0 mL, 10.1 mmol) at −40° C. The temperature was allowed to rise to −10° C. over 40 min then was lowered to −40° C. in an acetonitrile/dry ice bath. 3-Methyl-2-pyridinylmagnesium bromide (0.25M in THF, 20.2 mL, 5.0 mmol) was added dropwise and the solution was allowed to rise to rt over one hour. The solution was partitioned between satd ammonium chloride solution and DCM; organic extracts were concentrated then purified by silica gel column chromatography eluting with a gradient of 10-70% EtOAc in hexane to afford 2-amino-5-fluorophenyl)(3-methylpyridin-2-yl)methanone as a yellow oil: LC-MS (ESI) m/z 231.2 [M+H]+.

후처리

  1. customthen was lowered to −40° C. in an acetonitrile/dry ice bath
  2. waitto rise to rt over one hour
  3. customThe solution was partitioned between satd ammonium chloride solution and DCM
  4. concentrationorganic extracts were concentrated
  5. customthen purified by silica gel column chromatography
  6. washeluting with a gradient of 10-70% EtOAc in hexane

출처 및 근거

ORD 기록
ord-093185e68e544071a1aec297b85ac95c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765768B2

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