Sodium Hydroxide → 3-(1-(6-chloropyridazin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1H-indole

HRID 2274841Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=4)[N:15](S(C4C=CC=CC=4)(=O)=O)[CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=4)[NH:15][CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 3-(1-(6-chloropyridazin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole (Intermediate 44; 226 mg; 0.50 mmol) in THF (20 mL) was added NaOH (80 mg; 2.0 mmol). The reaction mixture was stirred at 75° C. for 16 hours, concentrated, and purified by preparative HPLC to afford 45 mg (28%) of the title compound as a yellow solid.

Workup

concentrationconcentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-5047e86cdf1c41f2a2dd13363d4d7c92
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126984B2

Reaction notes

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