Ethyl 4-piperidinecarboxylate → {2-[4-(Ethoxycarbonyl)piperidin-1-yl]pyrimidin-5-yl}boronic acid

HRID 626934

반응식

HRID 626934 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1>O1CCOCC1>[CH2:20]([O:19][C:17]([CH:14]1[CH2:15][CH2:16][N:11]([C:2]2[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=2)[CH2:12][CH2:13]1)=[O:18])[CH3:21]

참가 물질

4

반응물 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

생성물 1

HCID 131735233{2-[4-(Ethoxycarbonyl)piperidin-1-yl]pyrimidin-5-yl}boronic acid수율 51%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

(2-Chloropyrimidin-5-yl)boronic acid (2 g, 13 mmol) and ethyl piperidine-4-carboxylate (1.94 mL, 13 mmol) were dissolved in 1,4-dioxane (20 mL) and heated to 60° C. under microwave irradiation for 1 h. The reaction mixture was concentrated to dryness and partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to dryness, to afford the title compound (1.79 g, 51%) as a yellow gum. Method C HPLC-MS: MH+ m/z 280, RT 0.94 minutes (89%).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-887cd9ba4d444b31acc0b11e1d1fc50d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309243B2

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