Triacetoxyperiodinane → 1-(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-6-(morpholine-4-carbonyl)-1H-indol-3-yl) ethanone
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:31]=[N:32][C:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:45]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[O:46])[CH:43]=3)[C:38]([CH:53]([OH:55])[CH3:54])=[CH:37]2)=[N:34][CH:35]=1>ClCCl>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:35]=[N:34][C:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:45]([N:47]4[CH2:48][CH2:49][O:50][CH2:51][CH2:52]4)=[O:46])[CH:43]=3)[C:38]([C:53](=[O:55])[CH3:54])=[CH:37]2)=[N:32][CH:31]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dess-Martin periodinane reagent (437 mg, 1.008 mmol, 1.5 eq) was added at 0° C. to a stirred solution of (1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indol-6-yl)(morpholino)methanone (synthesis example 28, 300 mg, 0.672 mmol, 1.0 eq) in dichloromethane (10 mL). Stirring was continued for 2 h at room temperature and the reaction mixture was then filtered through a bed of celite. The celite was washed with dichloromethane (10 mL) and the filtrate was dried over anhydrous sodium sulfate and evaporated in vacuo. White solid. Yield: 250 mg (72% of theory).
Workup
- filtrationthe reaction mixture was then filtered through a bed of celite
- washThe celite was washed with dichloromethane (10 mL)
- dry with materialthe filtrate was dried over anhydrous sodium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-ad465f978c3841f0a5c332051036fd71
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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