Toluene → HCID 18693288, compound

HRID 1870725Notes

Reaction equation

HRID 1870725 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=3)[N:13]=[CH:12][C:11]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH:33]([C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH2:36]1)=[O:34].C1(C)C=CC=CC=1>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[CH:33]=[O:34])=[CH:17][CH:16]=3)[N:13]=[CH:12][C:11]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 15453914HCID 15453914, compoundHCID 86755583HCID 86755583, compound

Product 1

HCID 18693288HCID 18693288, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of ethyl 5-(2-morpholin-4-ylethoxy)-1-(4-bromophenyl)pyrazole-4-carboxylate (0.25 g, 0.59 mmol), sodium carbonate (0.20 g, 1.77 mmol), tetrakis(triphenylphosphine) palladium (0) (0.12 g, 0.18 mmol) and 1-formylbenzeneboronic acid (0.10 g, 0.76 mmol) in a solution of toluene (10 mL), ethanol (1 mL) and water (1 mL) was stirred at reflux for 18 h. The reaction was diluted with water and extracted with ethyl acetate. The organic extract was washed with brine and dried (Na2SO4). After removing the solvent, flash chromatography of the residue (silica gel, 50% ethyl acetate/hexane) afforded the title compound as an oil (0.14 g, 66%). 1H NMR (250 MHz, CDCl3) d 9.98 (s, 1H), 8.01 (d, 1H), 7.92 (s, 1H), 7.85 (d, 2H), 7.62 (d, 1H), 7.46 (m, 4H), 4.65 (t, 2H), 4.35 (q, 2H), 3.56 (t, 4H), 2.68 (t, 2H), 2.38 (t, 4H), 1.38 (t, 3H). MS(ESI) m/e 450.4 [M+H]+.

Workup

  1. temperatureat reflux for 18 h
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. customAfter removing the solvent, flash chromatography of the residue (silica gel, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0958f7bd1d5e4f5d998354c52bd52f6f
Source dataset
uspto-grants-2000_08
Patent number
US06100259

Reaction notes

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