Diisopropylethylamine → Benzyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate

HRID 2365466Notes

Reaction equation

HRID 2365466 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:18][C:19]1([CH3:35])[C:23]([CH3:25])([CH3:24])[O:22][B:21]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29](Cl)=[O:30])[O:20]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:24][C:23]1([CH3:25])[C:19]([CH3:18])([CH3:35])[O:20][B:21]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)=[O:30])[O:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98488Benzyl p-aminobenzoateHCID 578564183-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride

Product 1

HCID 57856434Benzyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoateYield 41.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzyl 4-aminobenzoate (4.39 g, 19.3 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride (4.30 g, 16.1 mmol) and N,N-diisopropylethylamine (7.49 g, 57.9 mmol) in methylene chloride (50 mL) was stirred at ambient temperature for 13 h. After this time, the reaction was concentrated under reduced pressure and purified by chromatography (silica, heptane to 1:3 ethyl acetate/heptane) to afford benzyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate (3.07 g, 78% pure by mass, 27% yield) as a light yellow sticky foam that was used without further purification.

Workup

  1. concentrationAfter this time, the reaction was concentrated under reduced pressure
  2. custompurified by chromatography (silica, heptane to 1:3 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-d32ee1df83364dea9f27d43ca4b51ee4
Source dataset
uspto-grants-2014_04
Patent number
US08697699B2

Reaction notes

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