Triethylamine → 2,2-Dimethyl-N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanamide

HRID 1910694Notes

Reaction equation

HRID 1910694 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[O:3]1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>N1C=CC=CC=1.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]=[CH:11][C:12]([NH:15][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13][CH:14]=2)[O:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 574164182,2-Dimethyl-N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanamideYield 57.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.5 g, 2.27 mmol), pivaloyl chloride (0.277 g, 2.20 mmol) and triethylamine (0.248 g, 2.45 mmol) in pyridine (10 mL) were stirred at room temperature overnight. The mixture was diluted with ethyl acetate and ice/water and the layers were separated. The aqueous phase was extracted with ethyl acetate and the combined extracts dried over sodium sulfate. Purification by chromatography (1:1 ethyl acetate in hexanes) gave the product (0.385 g, 56% yield) as a white solid. 1H-NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.23 (d, 1H), 8.06 (d, 2H), 1.33 (s, 12H), 1.31 (s, 9H). MS (ES+) m/z 305 (M+1).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined extracts dried over sodium sulfate
  4. customPurification by chromatography (1:1 ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8c2095e767c74d53a20f0a3ba0d69af9
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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