2-Aminopyridine → HCID 68443709, 화합물

HRID 331886노트

반응식

HRID 331886 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[CH2:19][C:20]1[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:22][O:23][C:24]=1[CH3:25]>C1COCC1.C(OCC)(=O)C>[CH3:25][C:24]1[O:23][N:22]=[C:21]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]=1[CH2:19][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 104392-AminopyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11052826Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-

생성물 1

HCID 68443709HCID 68443709, 화합물수율 18%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-aminopyridine (109 mg, 1.2 mmol) in THF (2 mL) was added potassium bis(trimethylsilyl)amide (0.9 M in THF, 1.2 mL, 1.1 mmol) at 0° C. under argon. After 10 min, a solution of 4-chloromethyl-5-methyl-3-phenyl-isoxazole (200 mg, 1.0 mmol) in THF (1 mL) was added and the resulting mixture stirred at 0° C. for 1 h. The mixture was then diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous phase was extracted with ethyl acetate and the combined extracts dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=4:1: to 1:1) afforded the title compound (45 mg, 18%) as an off white solid. MS: m/e=266.2 [M+H]+.

후처리

  1. washwashed with water (10 mL) and brine (10 mL)
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined extracts dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=4:1: to 1:1)

출처 및 근거

ORD 기록
ord-ebbe37abb20241489a6dd43910cb9ad7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877782B2

반응 노트

불러오는 중…