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

HRID 626934Notes

Reaction equation

HRID 626934 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(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%).

Workup

  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

Sources & evidence

ORD record
ord-887cd9ba4d444b31acc0b11e1d1fc50d
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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