Sodium hydride → HCID 89498377, compound

HRID 1778822Notes

Reaction equation

HRID 1778822 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:30])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([C:25]2[CH:26]=[N:27][NH:28][CH:29]=2)[O:19]1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:28]2[CH:29]=[C:25]([B:20]3[O:19][C:18]([CH3:30])([CH3:17])[C:22]([CH3:24])([CH3:23])[O:21]3)[CH:26]=[N:27]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 104927561-(Benzyloxy)-4-(bromomethyl)benzene

Product 1

HCID 89498377HCID 89498377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of EXAMPLE 4A (0.54 g) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.377 g) in N,N-dimethylformamide (5 mL) was cooled to 0° C. To this solution was added 60% sodium hydride (0.096 g). The solution was stirred at room temperature 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 with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 25% 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 with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ef57eb3f93e34eb8a6571a129ac6ab04
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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