2-Bromo-5-chloropyridine → HCID 178451146, 화합물

HRID 2207376노트

반응식

HRID 2207376 반응식
[Li]C(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[C:14]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH2:19][CH2:18]1)(=[O:16])[CH3:15]>C(Cl)Cl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH2:19][CH2:18]2)([OH:16])[CH3:15])=[N:8][CH:9]=1

참가 물질

5

반응물 3

HCID 8170982-Bromo-5-chloropyridineHCID 178418306HCID 178418306, 화합물HCID 178451155HCID 178451155, 화합물

생성물 1

HCID 178451146HCID 178451146, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

t-BuLi (0.950 mL, 1.52 mmol) was added dropwise to a cooled solution of 2-bromo-5-chloropyridine (225 mg, 1.17 mmol) in DCM (11 mL) at −78° C. over 2 minutes. The reaction mixture was stirred for 2 hours at −78° C. and a solution of butyl trans-4-acetylcyclohexanecarboxylate (291 mg, 1.286 mmol) in DCM (1 mL) was added dropwise at −78° C. The reaction mixture was slowly warmed to room temperature over a period of 16 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with DCM (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford trans-butyl 4-(1-(5-chloropyridin-2-yl)-1-hydroxyethyl)cyclohexanecarboxylate as a brown oil. MS ESI calc'd for C18H27ClNO3 [M+H]+ 340. found 340.

후처리

  1. temperatureThe reaction mixture was slowly warmed to room temperature over a period of 16 hours
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with DCM (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-1084353c6071462ca758614fd7cc31a9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376418B2

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