2-Amino-4-chloropyridine → HCID 178512052, 화합물

HRID 717555

반응식

HRID 717555 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=1.[CH:14]1([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=2)[C:22]#[N:23])[CH2:16][CH2:15]1>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:22](=[NH:23])[C:21]2[CH:24]=[C:17]([CH:14]3[CH2:16][CH2:15]3)[CH:18]=[N:19][CH:20]=2)[CH:8]=1

참가 물질

5

반응물 3

HCID 5818662-Amino-4-chloropyridineHCID 574196235-CyclopropylnicotinonitrileHCID 178418339Butyllithium

생성물 1

HCID 178512052HCID 178512052, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

n-Butyllithium (1.6 M, 2.2 mL, 0.0034 mol) was added slowly for a period of 5 min to a solution of 4-chloropyridin-2-amine (0.4 g, 0.0031 mol) in anhydrous tetrahydrofuran (20 mL) at −78° C. The reaction temperature was raised to −40° C. and stirred for 15 min. The reaction mixture was cooled to −78° C. and 5-cyclopropylnicotinonitrile (0.45 g, 0.0031 mol) in tetrahydrofuran (5 mL) was added. The temperature was raised to RT and stirred it for 3 h. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL) then extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was recrystalised with a DCM and ether mixture to afford the title compound. MS (M−1): 271.0.

후처리

  1. temperatureThe reaction mixture was cooled to −78° C.
  2. temperatureThe temperature was raised to RT
  3. stirringstirred it for 3 h
  4. customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL)
  5. extractionthen extracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customto afford the crude product, which
  9. customwas recrystalised with a DCM and ether mixture

출처 및 근거

ORD 기록
ord-d8c3e655819a4365bb6868c4d24a8396
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193724B2

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