Pyridine → 2-Bromo-N-[2-chloro-4-[[2,3-dihydro-2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]-5-methoxyphenyl]acetamide

HRID 1421515Notes

Reaction equation

HRID 1421515 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][N:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[O:12][C:11]2=[O:25])=[C:4]([O:26][CH3:27])[CH:3]=1.N1C=CC=CC=1.[Br:34][CH2:35][C:36](Br)=[O:37].[K+].[Br-]>C1COCC1>[Br:34][CH2:35][C:36]([NH:1][C:2]1[CH:3]=[C:4]([O:26][CH3:27])[C:5]([CH2:9][N:10]2[N:14]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:19][CH:20]=3)[O:12][C:11]2=[O:25])=[CH:6][C:7]=1[Cl:8])=[O:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 253877Potassium BromideHCID 161056143-[(4-Amino-5-chloro-2-methoxyphenyl)methyl]-5-[4-(trifluoromethyl) phenyl]-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 161056392-Bromo-N-[2-chloro-4-[[2,3-dihydro-2-oxo-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-3-yl]methyl]-5-methoxyphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-[(4-Amino-5-chloro-2-methoxyphenyl)methyl]-5-[4-(trifluoromethyl) phenyl]-1,3,4-oxadiazol-2(3H)-one (3 g, 7.5 mmol) and pyridine (0.68 ml, 8.41 mmol) were dissolved in THF (35 ml) under N2 and cooled to 0° C. Bromoacetyl bromide (0.72 ml, 8.26 mmol) was added dropwise and the reaction mixture stirred for 18 h at 24° C. before being partitioned between ethyl acetate (400 ml) and 0.1N HCl solution (50 ml). The organic phase was washed with saturated NaHCO3 solution and brine, and dried over MgSO4. Active carbon (500 mg) was added and the solution filtered through a plug of Celite. Concentration gave 3.8 g (98%); mp 140-182° C. (dec); IR(KBr, υ=cm-1) 3348, 2972, 1784, 1672, 1594, 1234, 1168, 1066; 1H NMR (300 MHz, DMSO-d6) δ 3.77 (3H, s), 4.15 (2H, s), 4.90 (2H, s), 7.47-7.48 (2H, m), 7.86 (2H, d, J=8.4 Hz), 7.96 (1H, d, J=8.3 Hz), 9.30 (1H, s); MS(ESl)m/z: 520(MH+)

Workup

  1. custombefore being partitioned between ethyl acetate (400 ml) and 0.1N HCl solution (50 ml)
  2. washThe organic phase was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. additionActive carbon (500 mg) was added
  5. filtrationthe solution filtered through a plug of Celite
  6. concentrationConcentration
  7. customgave 3.8 g (98%)

Sources & evidence

ORD record
ord-69d92ae7d0024f8e873fb74a49f0ac2c
Source dataset
uspto-grants-2000_06
Patent number
US06077861

Reaction notes

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