1-Naphthaleneboronic acid → HCID 67214354, compound

HRID 2421597Notes

Reaction equation

HRID 2421597 reaction equation
[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)[CH2:2][CH3:3].[C:14]1(B(O)O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>>[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:22]2[C:23]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:19]=[CH:20][CH:21]=2)[CH:7]=1)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 31186553-bromo-N-propylbenzamide

Product 1

HCID 67214354HCID 67214354, compoundYield 75%

Procedure

Using Preparation Method 2, N-n-propyl-3-bromobenzamide from Example 1A was reacted with 1-naphthylboronic acid. The resulting reaction mixture was purified using SiO2 with CH2Cl2/Petroleum ether 80:20 to CH2Cl2/AcOH 80:20 to give a thick yellow oil (75%). NMR 1H (ppm, CDCl3): 7.92-7.78 (m, 5H), 7.67-7.40 (m, 6H), 6.16 (br. s., 1H), 3.50-3.36 (m, 2H), 1.64 (sext., J3=7.33 Hz, 2H), 0.97 (t, J3=7.38 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-1bfe5cedfa704cc482b832d33f32d915
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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