Benzyl Bromide → HCID 86703335, compound

HRID 593260Notes

Reaction equation

HRID 593260 reaction equation
[NH2:1][C:2]1[C:3]([F:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C.O>[CH2:19]([NH:1][C:2]1[C:3]([F:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 55297322HCID 55297322, compound

Product 1

HCID 86703335HCID 86703335, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

As presented in the following reaction formula, a mixture of 5-amino-4-fluoro-2,3-dihydro-1H-inden-1-one (2.3 g, 14 mmol), cesium carbonate (Cs2CO3; 12 g, 28 mmol) and benzyl bromide (0.17 g, 72 mmol) in acetonitrile (CH3CN; 20 mL) was stirred under reflux for 48 hours. The mixture was concentrated to obtain the residue, which was dissolved in water (20 mL). The resulting solution was extracted three times with 20 mL of ethyl acetate. The combined organic phase was washed with saturated brine (50 mL), and dried and concentrated with anhydrous sodium sulfate to thereby give a crude product, which was purified by pre-TLC to give 5-(benzylamino)-4-fluoro-2,3-dihydro-1H-inden-1-one (370 mg, yield: 10%) as a yellow solid.

Workup

  1. temperatureunder reflux for 48 hours
  2. concentrationThe mixture was concentrated
  3. customto obtain the residue, which
  4. extractionThe resulting solution was extracted three times with 20 mL of ethyl acetate
  5. washThe combined organic phase was washed with saturated brine (50 mL)
  6. customdried
  7. concentrationconcentrated with anhydrous sodium sulfate
  8. customto thereby give a crude product, which
  9. customwas purified by pre-TLC

Sources & evidence

ORD record
ord-0bec00afdcb343b5b5471eeb9024b7c5
Source dataset
uspto-grants-2016_01
Patent number
US09242928B2

Reaction notes

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