Water → HCID 68550158, compound

HRID 731710Notes

Reaction equation

C([O:6][C:7]([C:11]1[C:12]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[N:13][N:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=12)=[C:8]([CH3:10])[CH3:9])(=O)C(C)C.FC1C=CC(C2C=C3C=CC(C(F)(F)F)=CN3N=2)=CC=1.O.[OH-].[Na+]>C(OC(=O)C(C)C)(=O)C(C)C.OS(O)(=O)=O>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:12]2[C:11]([C:7](=[O:6])[CH:8]([CH3:9])[CH3:10])=[C:15]3[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][N:14]3[N:13]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 142 °C

Procedure

1-(2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylprop-1-enyl isobutyrate. To 2.50 g (8.9 mmol) of 2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine in 43 ml of isobutyric anhydride was added conc. H2SO4 (5 drops). The mixture was stirred and heated at 142° C. overnight. The mixture was cooled to room temperature and poured into water (120 ml) at 0° C. The solution was then adjusted to pH 10 with 2N NaOH. The aqueous layer was extracted with Et2O (3×100 ml), dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography (3% EtOAc-hexane) to afford 2.54 g (68%) of the title compound) as an orange solid. Compound 1033.

Workup

temperatureThe mixture was cooled to room temperature
extractionThe aqueous layer was extracted with Et2O (3×100 ml)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash column chromatography (3% EtOAc-hexane)

Sources & evidence

ORD record: ord-2715ad5ef20a446089ba7cf714505b1b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585875B2

Reaction notes

Loading…