Potassium Bromide → HCID 57526267, compound

HRID 1452457Notes

Reaction equation

HRID 1452457 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([C:14]2[NH:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][C:22]([F:25])([F:24])[F:23])[N:15]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].[Br-]>C(OCC)(=O)C>[CH2:1]([C:8]1[CH:9]=[C:10]([C:14]2[N:19]=[CH:18][C:17](=[O:20])[N:16]([CH2:21][C:22]([F:25])([F:23])[F:24])[N:15]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 178516751HCID 178516751, compound

Product 1

HCID 57526267HCID 57526267, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(3-benzylphenyl)-1-(2,2,2-trifluoroethyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one (0.284 g, 0.8 mmol) and 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ, 0.204 g, 0.9 mmol) in ethyl acetate (9 mL) was refluxed for 5 hours, concentrated under reduced pressure, dissolved in methylene chloride (120 mL), washed with saturated aqueous sodium carbonate (2×60 mL), brine (70 mL), dried over magnesium sulfate and eluted through a silica gel plug. The filtrates were concentrated under reduced pressure to leave an amorphous yellow solid. Yield 0.267 g (95 percent). mp 95-96° C.; 1H NMR (CDCl3) δ 8.54 (s, 1H), 8.00 (s, 1H), 7.98 (d, J=9.0 Hz, 1H), 7.39 (t, J=7.5 Hz, 1H), 7.32-7.28 (m, 3H), 7.23-7.20(m, 3H), 4.76 (q, J=7.8 Hz, 2H), 4.06 (s, 2H); ES/MS 346 m/e (M+1); IR (KBr) σ cm−1 1688.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride (120 mL)
  3. washwashed with saturated aqueous sodium carbonate (2×60 mL), brine (70 mL)
  4. dry with materialdried over magnesium sulfate
  5. washeluted through a silica gel plug
  6. concentrationThe filtrates were concentrated under reduced pressure
  7. customto leave an amorphous yellow solid

Sources & evidence

ORD record
ord-7bdcac11edb945148088e700a30aa73d
Source dataset
uspto-grants-2009_01
Patent number
US07473669B2

Reaction notes

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