Dimethylformamide → HCID 22027852, compound

HRID 1519666Notes

Reaction equation

HRID 1519666 reaction equation
[H-].[Na+].CI.CN(C=O)C.[C:10]([O:14][C:15](=[O:32])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)=[CH:19][CH:18]=1)(C)(C)C>O.C(OCC)(=O)C>[CH3:10][O:14][C:15](=[O:32])[NH:16][C:17]1[CH:18]=[CH:19][C:20]([B:23]2[O:24][C:25]([CH3:30])([CH3:31])[C:26]([CH3:29])([CH3:28])[O:27]2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2734617tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate

Product 1

HCID 22027852HCID 22027852, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% Sodium hydride (0.55 g) and methyl iodide (1.2 mL) were added to a DMF (6.0 mL) solution of t-butyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (2.0 g), and the mixture was stirred for 18 hours at room temperature. Ethyl acetate and water were added to the reaction mixture, and the organic layer was isolated. The extract was washed sequentially with water and brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, whereafter the solvent was distilled off under reduced pressure. Hexane was added to the residue, and the precipitated solid was collected by filtration to obtain t-butyl=methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (white solid) (1.46 g, 70%).

Workup

  1. customthe organic layer was isolated
  2. washThe extract was washed sequentially with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThen, the desiccant was filtered out, whereafter the solvent
  5. distillationwas distilled off under reduced pressure
  6. additionHexane was added to the residue
  7. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ccd402d37948492bbe86e9a1d22ad661
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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