Hydrogen Bromide → 1-Bromo-7-fluoro-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-6-ol

HRID 2101129

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13]C)=[C:9]([F:12])[CH:10]=2)[CH:5]=[C:4]([NH:15][C:16]2[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=2)[N:3]=1.[BrH:22]>C(O)(=O)C>[Br:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[C:9]([F:12])[CH:10]=2)[CH:5]=[C:4]([NH:15][C:16]2[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=2)[N:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of (1-Chloro-7-fluoro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (1.0 g) in 10 mL acetic acid was added hydrobromic acid (1 mL, 40%). The mixture was heated at 160° C. for 30 min under microwave irradiation. Most of the solvent was removed under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate and washed with saturated sodium bicarbonate. The organic layer was dried with anhydrous sodium sulfate and concentrated to give oil (0.92 g), which was used for the next reaction without further purification. LC-MS m/e 338 (MH+).

Workup

customMost of the solvent was removed under reduced pressure
dissolutionthe residue was dissolved in 100 mL of ethyl acetate
washwashed with saturated sodium bicarbonate
dry with materialThe organic layer was dried with anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-f05aaaed1c3d4971a1f35e4749ef0c8c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572809B2

Linked notes

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