Diisopropylethylamine → Ethyl-2-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,3-oxazole-4-carboxylate

HRID 561239Notes

Reaction equation

HRID 561239 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Cl[C:17]1[O:18][CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=1.CCN(C(C)C)C(C)C>CCO>[CH2:25]([O:24][C:22]([C:20]1[N:21]=[C:17]([N:8]2[CH2:7][CH2:6][CH:5]([O:4][C:3]3[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:2]=3[Br:1])[CH2:10][CH2:9]2)[O:18][CH:19]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2763184Ethyl 2-chlorooxazole-4-carboxylateHCID 578327574-(2-Bromo-5-fluorophenoxy)piperidine

Product 1

HCID 66696829Ethyl-2-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,3-oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-bromo-5-fluorophenoxy)piperidine (3.281 g, 11.97 mmol) in EtOH (28.5 mL) was added ethyl 2-chlorooxazole-4-carboxylate (1 g, 5.70 mmol) and DIPEA (1.990 mL, 11.39 mmol). The reaction mixture was stirred at rt for 5 h. The solvent was evaporated under reduced pressure. The residue was diluted with 1N HCl and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-38931cb3ba214a42945869ec5193b004
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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