Potassium Phosphate, Tribasic → HCID 69896255, compound

HRID 1794284Notes

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.[CH3:26]B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[CH3:26][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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (100 mg) (prepared as in Example 4), methylboronic acid (72 mg), K3PO4 (276 mg), and dioxane (5 ml) was degassed with a stream of N2 for 0.5 h. tetrakis(triphenylphosphine) palladium(0) (20 mg) was added and the reaction heated to 80° C. for 1 h. The reaction mixture was cooled, poured into H2O and extracted into CH2Cl2, dried (MgSO4), and concentrated under reduced pressure to give the title compound (56 mg, 57%). 1H NMR (400 MHz, CDCl3) δ 7.82 (1H, s), 8.54–7.52 (2H, m), 7.47–7.37 (3H, m), 7.21 (1H, dd, J=7.8, 0.7 Hz), 7.14 (1H, d, J=8.0 Hz), 3.98 (2H, s), 2.70 (3H, s), 2.45 (3H, s), m/z (ES+) 329 (M+H)+.

Workup

customwas degassed with a stream of N2 for 0.5 h. tetrakis(triphenylphosphine) palladium(0) (20 mg)
additionwas added
temperatureThe reaction mixture was cooled
additionpoured into H2O
extractionextracted into CH2Cl2
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b9237c19e6dc45c2951348415d0629af
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022724B2

Reaction notes

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