Potassium Carbonate → HCID 86713095, compound

HRID 1774312Notes

Reaction equation

HRID 1774312 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:28]2[CH2:29][CH2:30][N:25]([C:20]3[C:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=4)=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:26][CH2:27]2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 71061917HCID 71061917, compound

Product 1

HCID 86713095HCID 86713095, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 2-bromo-1-(3-methoxyphenyl)ethanone (0.5 g, 2.2 mmol), 1-[3-(2-pyridyl)-2-pyridyl]piperazine (0.6 g, 2.6 mmol) and K2CO3 (3 mmol) in acetonitrile was refluxed overnight. After cooling, the mixture was evaporated to dryness and H2O (20 mL) was added to the residue. The aqueous phase was extracted with AcOEt (2×30 mL). The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/AcOEt, 9:1, as eluent) to afford pure compound in quantitative yield. 1H NMR (CDCl3): δ 2.52 (br s, 4H), 2.93 (app t, 4H), 3.78 (s, 2H), 3.80 (s, 3H), 6.84-6.90 (m, 3H), 7.04-7.10 (m, 2H) 7.20-7.26 (m, 1H), 7.71 (dd, 1H, J=1.6, 7.4 Hz), 7.83 (dt, 1H, J=1.9, 7.4 Hz), 7.88-7.92 (m, 1H), 8.27 (dd, 1H, J=1.9, 4.9 Hz), 8.69-8.72 (m, 1H). GC-MS m/z 387 (M+1, 2), 390 (M+, 8), 254 (100), 184 (63).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness and H2O (20 mL)
  4. additionwas added to the residue
  5. extractionThe aqueous phase was extracted with AcOEt (2×30 mL)
  6. dry with materialThe collected organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude residue was chromatographed (CHCl3/AcOEt, 9:1, as eluent)
  9. customto afford pure compound in quantitative yield

Sources & evidence

ORD record
ord-a56bbae43ca44ebb880de4f23d0a35cd
Source dataset
uspto-grants-2016_02
Patent number
US09260400B2

Reaction notes

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