Trifluoromethanesulfonic anhydride → Trifluoromethanesulfonic acid 5-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-yl ester

HRID 1890931Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:16]([OH:17])=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH:4]=[N:3]1.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20]>N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:16]([O:17][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:18])=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

5-(1-Methyl-1H-pyrazol-4-yl)-quinolin-6-ol (2.9 g, 12.89 mmol) was dissolved in pyridine (30 mL) and the mixture was cooled to 0° C. in an ice bath under a flow of nitrogen. Tf2O (2.6 mL, 15.47 mmol) was added slowly. Then the reaction mixture was stirred at room temperature for 5 hours. The mixture was partitioned between dichloromethane (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic phase was separated and washed with brine (5×30 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3.9 g of Trifluoromethanesulfonic acid 5-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-yl ester (84% yield): 1H NMR (300 MHz, CDCl3) δ: 4.05 (s, 3H), 7.48˜7.44 (m, 1H), 7.69˜7.61 (m, 3H), 8.18 (d, 1H), 8.32 (m, 1H), 8.98 (m, 1H); MS (m/z) 358 [M+H]+.

Workup

customThe mixture was partitioned between dichloromethane (50 mL) and saturated aqueous NaHCO3 (50 mL)
customThe organic phase was separated
washwashed with brine (5×30 mL)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-3ffe44dfb84e4da994599fe3c359d784
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507489B2

Reaction notes

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