Water → HCID 68208418, compound

HRID 1026387Notes

Reaction equation

HRID 1026387 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:14][C:5]2[NH:6][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:8][C:4]=2[CH2:3]1.[H-].[Na+].Br[CH2:19][C:20]#[N:21].O>CN(C=O)C.C(OCC)(=O)C>[C:20]([CH2:19][N:6]1[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:8][C:4]2[CH2:3][C:2]([CH3:1])([CH3:15])[CH2:14][C:5]1=2)#[N:21]

Participants

7

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 68096415ETHYL 5,5-DIMETHYL-1,4,5,6-TETRAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLATE

Product 1

HCID 68208418HCID 68208418, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 250-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 103b)(6.2 g, 30 mmol) in DMF (57 mL). To the solution was added NaH (80% dispersion in mineral oil, 1.26 g, 42.1 mmol). The resulting mixture was stirred at rt for 90 min. After that time, bromoacetonitrile (2.94 mL, 42 mmol) was added. The mixture was stirred for 14 h. After that time, water (100 mL) and ethyl acetate (200 mL) were added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to afford a 95% yield (7 g) of 103c.

Workup

  1. customA 250-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. stirringThe mixture was stirred for 14 h
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-987b27ce0ea241a282e1b3eb6cf9dc1b
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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