Sodium hydride → HCID 86681255, compound

HRID 588653Notes

Reaction equation

HRID 588653 reaction equation
[Br:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH2:12]Br)([CH2:5]3)[CH2:3]1)[CH2:9]2.[I:14][C:15]1[CH:16]=[N:17][NH:18][CH:19]=1.[H-].[Na+]>CN(C)C=O>[Br:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH2:12][N:17]4[CH:16]=[C:15]([I:14])[CH:19]=[N:18]4)([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 770224-IodopyrazoleHCID 27697121-Bromo-3-(bromomethyl)adamantane

Product 1

HCID 86681255HCID 86681255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-bromo-3-(bromomethyl)-adamantane (1.0 g) and 4-iodopyrazole (0.63 g) in N,N-dimethylformamide (10 mL) was cooled to 0° C. To this solution was added 60% sodium hydride (0.20 g). The solution was stirred at 65° C. overnight. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed three times with water, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10% ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  3. washThe combined organic layers were washed three times with water
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel eluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6a4c23a4ce144272893bb842d4a545f2
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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