Cesium carbonate → HCID 69895797, compound

HRID 1794283Notes

Reaction equation

HRID 1794283 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]3[C:13]([C:14]4[C:15]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[N:16][O:17][C:18]=4[CH3:19])=[N:12][N:11]=[C:8]32)=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][C:29](OB=O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]=1[C:13]1[N:7]2[CH2:6][C:5]3[C:9]([C:8]2=[N:11][N:12]=1)=[CH:10][C:2]([C:29]1[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=1)=[CH:3][CH:4]=3

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10000630HCID 10000630, compoundHCID 22220925HCID 22220925, compound

Product 1

HCID 69895797HCID 69895797, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (220 mg) (prepared as in Example 4), 4-pyridylboranic acid (295 mg), Cs2CO3 (1.26 g/l ml H2O), and DME (3 ml) was degassed with a stream of N2 for 0.5 h. Bis(triphenylphosphine)palladium(II) chloride (42 mg) was added and the reaction heated to 100° C. for 5 h. The reaction mixture was cooled, poured into H2O and extracted into CH2Cl2, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica, eluting with 3% MeOH/CH2Cl2, and recrystallised from CH2Cl2/hexane to give the title compound (50 mg, 21%). 1H NMR (360 MHz, CDCl3) δ 8.72 (2H, d, J=4.5 Hz), 8.29 (1H, d, J=1.3 Hz), 7.67 (1H, dd, J=8.0, 1.7 Hz), 7.57–7.53 (4H, m), 7.48–7.39 (4H, m), 4.07 (2H, s), 2.73 (3H, s), m/z (ES+) 392 (M+H)+.

Workup

  1. customwas degassed with a stream of N2 for 0.5 h
  2. additionBis(triphenylphosphine)palladium(II) chloride (42 mg) was added
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into H2O
  5. extractionextracted into CH2Cl2
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica
  9. washeluting with 3% MeOH/CH2Cl2
  10. customrecrystallised from CH2Cl2/hexane

Sources & evidence

ORD record
ord-26e9abdfc80640238a6851f67a3c1e1b
Source dataset
uspto-grants-2006_04
Patent number
US07022724B2

Reaction notes

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