4-Fluorophenylboronic acid → HCID 67214260, compound

HRID 2421601Notes

Reaction equation

HRID 2421601 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].[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)[CH:7]=1)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 31186553-bromo-N-propylbenzamide

Product 1

HCID 67214260HCID 67214260, compoundYield 70%

Procedure

Using Preparation Method 2, N-n-propyl-3-bromobenzamide from Example 1A as reacted with 4-fluorophenylboronic acid. The resulting reaction mixture was purified using SiO2 with CH2Cl2/Petroleum Ether 80:20 to CH2Cl2/Ethyl Acetate 80:20 to give a white solid (70%). NMR 1H (ppm, CDCl3): 7.94 (t, J4=2.1 Hz, 1H), 7.66 (tt, J3=7.8 Hz, J4=0.9 Hz, 2H), 7.58-7.53 (m, 2H), 7.47 (t, J3=7.8 Hz, 1H), 7.13 (t, J3=9 Hz, 2H), 6.12 (br. s., 1H), 3.47-3.40 (m, 2H), 1.65 (sext., J3=7.5 Hz, 2H), 0.99 (t, J3=7.44 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-c63191072a0448ce931b81907ab33def
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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