Sodium Carbonate → HCID 22459291, compound

HRID 355742Notes

Reaction equation

HRID 355742 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14](Br)=[C:13]([CH3:18])[CH:12]=2)=[CH:5][C:4]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].[S:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1>O.COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([C:35]3[CH:36]=[CH:37][S:33][CH:34]=3)=[C:13]([CH3:18])[CH:12]=2)=[CH:5][C:4]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 117962574-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-3-methylbenzamide

Product 1

HCID 22459291HCID 22459291, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(4Methoxy-3-(4-methyl-1-piperazinyl)phenyl)-4-bromo-3-methylbenzamide (0.35 g, 0.84 mmol), sodium carbonate (89 mg, 0.84 mmol), tetrakis (triphenylphosphine)palladium(0) (49 mg, 0.05 equiv), 3-thiophenyl boronic acid (115 mg, 0.84 mmol) in water (18 ml) and DME (18 ml) were heated at reflux under argon for 18 h. The solution was partitioned between saturated aqueous potassium carbonate solution (50 ml) and chloroform (50 ml), the organic extracts dried (sodium sulphate), filtered and evaporated to dryness under reduced pressure. The resulting oil was purified by column chromatography (silica, chloroform/methanol 5-30%) to afford the tide compound as an oil (242 mg, 63%) which was crystallised as an oxalate salt from methanol chloroform.

Workup

  1. temperatureat reflux under argon for 18 h
  2. customThe solution was partitioned between saturated aqueous potassium carbonate solution (50 ml) and chloroform (50 ml)
  3. dry with materialthe organic extracts dried (sodium sulphate)
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customThe resulting oil was purified by column chromatography (silica, chloroform/methanol 5-30%)

Sources & evidence

ORD record
ord-f80a96c18a834c2286de3754b93e1321
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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