Potassium Carbonate → 3-[5-Bromo-2-(5-trifluoromethyl-furan-2-ylmethoxy)-benzyl]-azetidine

HRID 237303Notes

Reaction equation

HRID 237303 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][C:21]2[O:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)=[C:6]([CH:18]=1)[CH2:7][CH:8]1[CH2:11][N:10](C(=O)C(F)(F)F)[CH2:9]1.C([O-])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][C:21]2[O:22][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:24][CH:25]=2)=[C:6]([CH:18]=1)[CH2:7][CH:8]1[CH2:11][NH:10][CH2:9]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866570631-{3-[5-Bromo-2-(5-trifluoromethyl-furan-2-ylmethoxy)-benzyl]-azetidin-1-yl}-2,2,2-trifluoro-ethanone

Product 1

HCID 462149743-[5-Bromo-2-(5-trifluoromethyl-furan-2-ylmethoxy)-benzyl]-azetidineYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-{3-[5-bromo-2-(5-trifluoromethyl-furan-2-ylmethoxy)-benzyl]-azetidin-1-yl}-2,2,2-trifluoro-ethanone (76 mg, 0.16 mmol) in methanol (10 mL) was added K2CO3 (94 mg, 0.70 mmol). After 1 h, TLC analysis indicated complete consumption of the starting material. Brine and EtOAc were added to the reaction mixture and the aqueous portion was extracted with EtOAc (3×). The combined organic layers were dried. The crude product was purified by RP HPLC (basic conditions) to provide the title compound (50 mg, 76%). MS (ESI): mass calcd. for C16H15BrF3NO2, 390.2; m/z found, 393.2 [M+H]+. 1H NMR (CDCl3): 7.50-7.41 (m, 1H), 7.35-7.26 (m, 1H), 6.89-6.79 (m, 2H), 6.53 (s, 1H), 5.05 (s, 2H), 4.43-4.20 (m, 1H), 3.63 (t, J=8.2 Hz, 2H), 3.44 (t, J=7.7 Hz, 2H), 2.85 (d, J=7.6 Hz, 2H).

Workup

  1. customconsumption of the starting material
  2. additionBrine and EtOAc were added to the reaction mixture
  3. extractionthe aqueous portion was extracted with EtOAc (3×)
  4. customThe combined organic layers were dried
  5. customThe crude product was purified by RP HPLC (basic conditions)

Sources & evidence

ORD record
ord-7270c15a0a9741d5aa5e419daaa86ab7
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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