tert-Butanol → N-(4-chloro-5-formylpyridin-2-yl)acetamide

HRID 2369530노트

반응식

HRID 2369530 반응식
[Cl:1][C:2]1[C:7]([CH:8]=C)=[CH:6][N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1.N1C(C)=CC=CC=1C.CC([OH:26])(C)C.I([O-])(=O)(=O)=O.[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[C:7]([CH:8]=[O:26])=[CH:6][N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1

참가 물질

8

반응물 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 86695930N-(4-chloro-5-vinylpyridin-2-yl)acetamide

생성물 1

HCID 86695931N-(4-chloro-5-formylpyridin-2-yl)acetamide수율 92.1%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of N-(4-chloro-5-vinylpyridin-2-yl)acetamide (6 g, 30.5 mmol) and 2,6-lutidine (7.11 mL, 61.0 mmol) in a mixture of dioxane (110 mL) and water (25 mL) at 0° C. was added osmium tetroxide, 2.5 wt % solution in 2-methyl-2-propanol (9.58 mL, 30.5 mmol) followed by the addition of sodium periodate (19.58 g, 92 mmol) and the reaction was stirred for 4 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine solution, dried over sodium sulphate, concentrated under reduced pressure. The residue was purified by silica column using hexane/Ethyl acetate to yield N-(4-chloro-5-formylpyridin-2-yl)acetamide as an off-white solid (5.8 g, 28.1 mmol, 92% yield). LCMS (ESI) m/e 197.0 [(M)−, calcd for C8H6ClN2O2197.04] LC/MS retention time (method A): tR=1.21 min; 1H NMR (400 MHz, DMSO-d6) δ 11.20 (s, 1H), 10.18 (s, 1H), 8.76 (s, 1H), 8.27 (s, 1H), 2.16 (s, 3H).

후처리

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic layers were washed with brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica column

출처 및 근거

ORD 기록
ord-e729132a23bb49a7959839782c6275e2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703953B2

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