2-Aminopyridine → 3-Chloro-4-((pyridin-2-ylamino)methyl)benzaldehyde

HRID 1502861노트

반응식

HRID 1502861 반응식
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[Cl:11].C([O-])([O-])=O.[K+].[K+].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C(=O)C.O>[Cl:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH2:2][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH:7]=[O:8]

참가 물질

6

반응물 3

HCID 104392-AminopyridineHCID 11430Potassium CarbonateHCID 866751774-(Bromomethyl)-3-chlorobenzaldehyde

생성물 1

HCID 866751823-Chloro-4-((pyridin-2-ylamino)methyl)benzaldehyde수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

To a stirred solution of 4-(bromomethyl)-3-chlorobenzaldehyde (2 g, 9 mmol) in N,N-dimethylacetamide (DMA; 20 mL) was added K2CO3 (2.36 g, 17.16 mmol) and 2-aminopyridine (0.84 g, 8.58 mmol), and the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography (SiO2, 100-200 mesh; 20% EtOAc in n-Hexane) to afford the title compound as off-white solid (1.05 g, 50%): mp 122-123° C.; 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 8.11 (s, 1H), 7.88 (s, 1H), 7.72 (d, J=4.8 Hz, 1H), 7.62 (d, J=5.7 Hz, 1H), 7.4 (m, 1H), 6.64 (d, J=3.9 Hz, 1H), 6.38 (d, J=6.3 Hz, 1H), 5.04 (br s, 1H), 4.71 (s, 2H); ESIMS m/z 246.97 ([M+H]+).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (SiO2, 100-200 mesh; 20% EtOAc in n-Hexane)

출처 및 근거

ORD 기록
ord-0d97c86ad2bd4497a1677c016641c0c7
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09211280B2

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