Triethylamine → N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,4-dioxane-2-carboxamide

HRID 1852905Notes

Reaction equation

HRID 1852905 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[O:3]1.C(N(CC)CC)C.[O:24]1[CH2:29][CH2:28][O:27][CH2:26][CH:25]1[C:30](Cl)=[O:31]>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[C:11]([NH:12][C:30]([CH:25]3[CH2:26][O:27][CH2:28][CH2:29][O:24]3)=[O:31])[CH:13]=[CH:14][CH:15]=2)[O:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 628040161,4-Dioxane-2-carbonyl chloride

Product 1

HCID 71138628N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,4-dioxane-2-carboxamideYield 81%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (220 mg) and triethylamine (0.182 mL) in N,N-dimethylacetamide (1.5 mL) chilled to 0° C. was added 1,4-dioxane-2-carbonyl chloride (prepared from 1,4-dioxane-2-carboxylic acid (159 mg) and oxalyl chloride (0.15 mL) in dichloromethane (2.5 mL)) dropwise. After being stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate and washed with 1 M citric acid aqueous solution (3 times) then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-100% ethyl acetate in hexanes) gave the product (270 mg, 81%).

Workup

  1. washwashed with 1 M citric acid aqueous solution (3 times)
  2. dry with materialThe organics were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by column chromatography (10-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c1dc69f4f39541909e51b0761b1f2c95
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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