Ethanol → 6-Fluoro-5-(hydroxymethyl)indolin-2-one
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[C:12](OC)=[O:13].CCO.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[CH2:12][OH:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of the compound obtained in Step B (2.68 mmoles) in anhydrous THF (20 mL) is maintained under nitrogen in the presence of 0.3 mL of EtOH. The solution is cooled to 0° C. and then 5.28 mmol of LiBH4 are added. The reaction mixture is stirred for 2 hours at ambient temperature; a second portion of LiBH4 (6.20 mmol) is then added and stirring is maintained for a further 3 hours. EtOH (0.3 mL) and a third portion of LiBH4 (9.14 mmol) are added and the reaction mixture is stirred overnight. The reaction mixture is quenched with 10 mL of water, and then saturated aqueous NH4Cl solution (30 mL) is added. Extraction with EtOAc is carried out, and the organic phases are dried over Na2SO4, filtered and evaporated in vacuo. The residue obtained is purified by flash chromatography (DCM/MeOH 10:1) to yield the title product.
Workup
- stirringstirring
- temperatureis maintained for a further 3 hours
- stirringthe reaction mixture is stirred overnight
- customThe reaction mixture is quenched with 10 mL of water
- additionsaturated aqueous NH4Cl solution (30 mL) is added
- extractionExtraction with EtOAc
- dry with materialthe organic phases are dried over Na2SO4
- filtrationfiltered
- customevaporated in vacuo
- customThe residue obtained
- customis purified by flash chromatography (DCM/MeOH 10:1)
Sources & evidence
- ORD record
- ord-713b5aa830674ea7a05e83acffd77223
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653073B2
Reaction notes
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