Water → HCID 58110594, compound

HRID 2096999Notes

Reaction equation

HRID 2096999 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[CH2:16][C:15]1[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 130983864-Bromo-2,3-dihydro-1H-indole

Product 1

HCID 58110594HCID 58110594, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-bromoindoline (200 mg, 1.00 mmol) in 5 ml DMF was added 4-Fluorobenzylbromide (0.14 ml, 1.1 mmol) then add NaH (40 mg, 1.0 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 280 mg (92%) of product.

Workup

  1. extractionextract three times with EtOAc
  2. washPool all organics and wash one time with brine
  3. dry with materialthen dry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate to dryness
  6. customThe residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50)

Sources & evidence

ORD record
ord-4141a248bdbc4947b9794c6f371ebc4f
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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