4-Methyl-3-cyanopyridine → HCID 178428388, 화합물

HRID 717551

반응식

HRID 717551 반응식
C([Li])CCC.[F:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1.[CH3:14][C:15]1[C:20]([C:21]#[N:22])=[CH:19][N:18]=[CH:17][CH:16]=1>O1CCCC1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:21](=[NH:22])[C:20]2[C:15]([CH3:14])=[CH:16][CH:17]=[N:18][CH:19]=2)=[N:11][CH:12]=1

참가 물질

5

반응물 3

HCID 2278064-Methyl-3-cyanopyridineHCID 27377012-Amino-5-fluoropyridineHCID 178418339Butyllithium

생성물 1

HCID 178428388HCID 178428388, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

n-Butyllithium (1.6 M, 3.33 mL, 0.00534 mol) was added slowly for a period of 5 min at a temperature of at −78° C. to a solution of 5-fluoro-pyridin-2-ylamine (0.3 g, 0.00267 mol) in anhydrous tetrahydrofuran (20 mL). Then the temperature raised to −40° C. and the reaction mixture was stirred for 15 min. The reaction mixture was cooled to −78° C. and 4-methyl-nicotinonitrile (0.316 g, 0.00267 mol) in tetrahydrofuran (5 mL) was added. The temperature was raised to RT and stirred for 18 h. The reaction mixture quenched with a saturated aqueous ammonium chloride solution (25 mL) and then extracted with ethyl acetate (2×50 mL). The combined organic layer were dried over sodium sulphate and concentrated under vacuum to afford the crude product, N-(5-fluoro-pyridin-2-yl)-4-methyl-nicotinamidine, which was used without further purification in the next step. MS (M+1): 231.1.

후처리

  1. temperatureThe reaction mixture was cooled to −78° C.
  2. temperatureThe temperature was raised to RT
  3. stirringstirred for 18 h
  4. customThe reaction mixture quenched with a saturated aqueous ammonium chloride solution (25 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic layer were dried over sodium sulphate
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-8d9aaf713f88455a863121813b28adae
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193724B2

연결된 노트

불러오는 중…