Sodium Bicarbonate → 1-(2-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)ethyl)imidazolidin-2-one

HRID 2274802Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.CS(O[CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][NH:34][C:33]1=[O:37])(=O)=O.C([O-])(O)=O.[Na+]>CCO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:24]=[N:23][N:22]([CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][NH:34][C:33]4=[O:37])[CH:21]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 300 mg; 0.88 mmol), 2-(2-oxoimidazolidin-1-yl)ethyl methanesulfonate (Intermediate 31; 274 mg; 1.32 mmol), NaHCO3 (403 mg; 4.80 mmol) in EtOH (10 mL) was stirred at 90° C. overnight. The reaction mixture was concentrated, diluted with EtOAc (30 mL), washed with water (30 mL), brine (30 mL), dried over anhydrous Na2SO4, filtered, and concentrated to afford 100 mg (25%) of the title compound as a yellow solid, which was used directly used without further purification.

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with EtOAc (30 mL)
washwashed with water (30 mL), brine (30 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-071748a828e348ef91810f64f42e4765
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126984B2

Reaction notes

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