2,5-Dibromopyridine → tert-Butyl 4-((5-bromopyridin-2-yl)amino)piperidine-1-carboxylate

HRID 1627557노트

반응식

HRID 1627557 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

참가 물질

5

반응물 3

HCID 693532,5-DibromopyridineHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidine

생성물 1

HCID 53439130tert-Butyl 4-((5-bromopyridin-2-yl)amino)piperidine-1-carboxylate수율 10.1%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

A tube was charged with 2,5-dibromopyridine (0.24 g, 1.0 mmol), 4-Amino-piperidine-1-carboxylic acid tert-butyl ester (0.22 g, 1.1 mmol), di-isopropylethylamine (0.19 mL, 1.1 mmol) and N-methylpyrrolidinone (1.0 mL). The tube was sealed and the mixture was heated at 80° C. overnight. The temperature was increased to 120° C. and heated overnight. The reaction was partitioned between ethyl acetate and water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of ethyl acetate and hexanes to afford 4-(5-bromo-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (36 mg, 10%).

후처리

  1. customThe tube was sealed
  2. temperatureThe temperature was increased to 120° C.
  3. temperatureheated overnight
  4. customThe reaction was partitioned between ethyl acetate and water
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by silica gel chromatography
  10. washelution of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-94bf8bf1e991489dbb1b810d9372ea8a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785632B2

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