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

HRID 1627557ノート

反応式

HRID 1627557 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-94bf8bf1e991489dbb1b810d9372ea8a
出典データセット
uspto-grants-2014_07
特許番号
US08785632B2

反応ノート

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