Cesium carbonate → 6-Bromo-1-(3-fluorobenzyl)indoline

HRID 871073

Reaction equation

HRID 871073 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 130983796-Bromo-2,3-dihydro-1H-indole

Product 1

HCID 904086526-Bromo-1-(3-fluorobenzyl)indoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromoindoline (750 mg, 3.79 mmol), 1-(bromomethyl)-3-fluorobenzene (697 pt, 5.68 mmol) and cesium carbonate (1.851 g, 5.68 mmol) in N,N-dimethylformamide (7.573 mL) was stirred at 110° C. for 2 hours. The mixture was cooled, diluted with 100 mL ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco®, Redi-Sep® column), eluting with a gradient of 2-50% ethyl acetate/hexane, afforded the title compound. LCMS: 306 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel flash chromatography (Isco®, Redi-Sep® column)
  7. washeluting with a gradient of 2-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-88a32b9c0dec4ded89645f7fd044b689
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Linked notes

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