Hydrochloric Acid → Ethyl 5-(2-fluoro-4-methoxyphenyl)-6-methyl-1H-indazole-3-carboxylate

HRID 1054803Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7](COCC[Si](C)(C)C)[N:8]=[C:9]2[C:14]=1[CH:13]=[C:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[F:23])[C:11]([CH3:24])=[CH:10]2)=[O:5])[CH3:2].Cl>CCO>[F:23][C:16]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[CH3:24])[NH:8][N:7]=[C:6]2[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-(2-fluoro-4-methoxyphenyl)-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-3-carboxylic acid ethyl ester (440 mg, 0.96 mmol) in EtOH (6 mL) was added 3 N HCl solution (1.5 mL, 4.5 mmol). The reaction mixture was heated to 90° C. for 1 hour, cooled to room temperature and concentrated in vacuo. The residue was partitioned between water and EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound (292 mg, 93% yield) as an amber color solid. MS (ES+) 329.3 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.06 (s, 1H), 7.48 (s, 1H), 7.22 (t, J=8.54 Hz, 1H), 6.81 (dd, J=8.54, 1.95 Hz, 1H), 6.75 (d, J=11.47 Hz, 1H), 4.52 (q, J=7.16 Hz, 2H), 3.89 (s, 3H), 2.34 (s, 3H), 1.47 (t, J=7.07 Hz, 3H).

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customThe residue was partitioned between water and EtOAc
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-209875ee459f4ea2974a53d8f007eeab
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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