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

HRID 626934ノート

反応式

HRID 626934 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-887cd9ba4d444b31acc0b11e1d1fc50d
出典データセット
uspto-grants-2016_04
特許番号
US09309243B2

反応ノート

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