Potassium Hydroxide → 6-(2-Methoxyphenyl)-2-(4-(trifluoromethyl)phenyl)-1,2-dihydroindazol-3-one

HRID 270689Notes

Reaction equation

Cl[C:2]1[N:3]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[CH:6]2.[OH-:29].[K+]>CO>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:7]1[CH:6]=[C:5]2[C:10]([C:2](=[O:29])[N:3]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[NH:4]2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 160 °C

Procedure

The product of Step 1 (100 mg) was dissolved in 1N KOH in MeOH (2 mL) and heated at 160° C. for 2 min via microwave irradiation. The resulting yellow solution was concentrated, diluted with water and acidified with 2N HCl. The precipitate was collected and recrystallised from EtOH/H2O to give 21 mg of product as colourless needles. 1H NMR (500 MHz, DMSO): 3.81 (3H, s), 7.08 (1H, t, J 7.4 Hz), 7.18 (1H, d J 7.4 Hz), 7.31 (1H, dd, J 1.2 and 8.0 Hz), 7.38 (1H, dd, J 1.2 and 8.0 Hz), 7.39-7.42 (1H, m), 7.44 (1H, s), 7.79 (1H, d, J 8.0 Hz). 7.89 (2H, d, J 8.5 Hz), 8.18 (2H, d, J 8.5 Hz), 10.76 (1H, s).

Workup

concentrationThe resulting yellow solution was concentrated
additiondiluted with water
customThe precipitate was collected
customrecrystallised from EtOH/H2O

Sources & evidence

ORD record: ord-4a5e8a1db71d478fbf2cf7c9357d6558
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449585B2

Reaction notes

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