Diisopropylethylamine → N-(2-(pyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1410028Notes

Reaction equation

HRID 1410028 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]3)=[CH:17][CH:16]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 832754-PyridineethanamineHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68379398N-(2-(pyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 118.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (150 mg, 0.60 mmol) in 30 mL of DCM were added 2-(pyridin-4-yl)ethanamine (110 mg, 0.9 mmol), HATU (274 mg, 0.72 mmol) and DIEA (232 mg, 1.80 mmol) at room temperature. Then the reaction mixture was stirred at room temperature overnight. The solution was washed with sat NaHCO3 (2×20 mL), brine (20 mL), then dried over anhydrous sodium sulfate, concentrated under reduce pressure to give crude N-(2-(pyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (250 mg) and used without further purification. LC-MS: 353 [M+H]+, tR=1.22 min

Workup

  1. washThe solution was washed with sat NaHCO3 (2×20 mL), brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dd385cf7f9354c208f053387f3070f41
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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