Sodium Iodide → 6-fluoro-3-(1-(2-(4-methylpiperazin-1-yl)ethyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-indole

HRID 2274803Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=3)[N:11]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:10]=2)[CH:6]=[N:5]1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[F:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9]([C:7]3[CH:6]=[N:5][N:4]([CH2:3][CH2:2][N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)[CH:8]=3)=[CH:10][N:11]2[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(1-(2-bromoethyl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole (Intermediate 22; 100 mg; 0.22 mmol) in MeCN (10 mL) was added 1-methylpiperazine (44 mg; 0.44 mmol), K2CO3 (62 mg; 0.45 mmol), and NaI (33 mg; 0.22 mmol). The mixture was stirred at 80° C. for 4 hours, filtered, concentrated, and purified by preparative TLC (DCM/MeOH=10/1) to afford 70 mg (68%) of the title compound as a yellow solid.

Workup

filtrationfiltered
concentrationconcentrated
custompurified by preparative TLC (DCM/MeOH=10/1)

Sources & evidence

ORD record: ord-2db5dabc2aef461db4a392d9d3a16cef
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126984B2

Reaction notes

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