Sodium hydride → HCID 68526680, compound

HRID 2246721Notes

Reaction equation

HRID 2246721 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:2]1=[O:15].[H-].[Na+].[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>CN(C)C=O>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:2]1=[O:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 12888301Spiro[cyclohexane-1,3'-indolin]-2'-one

Product 1

HCID 68526680HCID 68526680, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Spiro[cyclohexane-1,3′-indol]-2′(1′H)-one (1.0 g, 5 mmol) was dissolved in dimethylformamide (10 mL) and NaH (0.21 g, 5.5 mmol) was added and the mixture was stirred 30 minutes then 3-fluorobenzyl bromide (1.04 g, 5.5 mmol) was added. The mixture was stirred 2 hours then quenched with saturated aqueous ammonium chloride, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 0-20% ethyl acetate in hexane) to afford 0.8 g of 1′-(3-fluorobenzyl)spiro[cyclohexane-1,3′-indol]-2′(1′H)-one.

Workup

  1. stirringThe mixture was stirred 2 hours
  2. customthen quenched with saturated aqueous ammonium chloride
  3. additiondiluted with ether
  4. washwashed with water, and saturated brine
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1721f37a3794433686db6f0355315aa4
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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