(Pyridin-4-yl)boronic acid → 2-[3-Methoxy-4-(pyridin-4-ylmethyl)phenyl]-1,3-benzoxazole

HRID 7752Notes

Reaction equation

HRID 7752 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH:6]=[CH:7][C:8]=1[CH2:9]C1C=NC=CC=1.BrCC1C=CC(C2OC3[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=3[N:37]=2)=CC=1OC.N1C=CC(B(O)O)=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][C:39]1[CH:38]=[CH:36][N:37]=[CH:41][CH:40]=1

Participants

4

Reactant 3

HCID 2734379(Pyridin-4-yl)boronic acidHCID 102366482-[3-Methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazoleHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Product 1

HCID 102366472-[3-Methoxy-4-(pyridin-4-ylmethyl)phenyl]-1,3-benzoxazole

Procedure

Utilizing the general procedure outlined for 2-[3-methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (270 mg, 0.81 mmol), 4-pyridylboronic acid (100 mg, 0.81 mmol) reacted to afford the desired 2-[3-methoxy-4-(pyridin-4-ylmethyl)phenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.46 (br s, 2H), 7.75–7.81 (m, 3H), 7.56–7.59 (m, 1H), 7.34–7.36 (m, 2H), 7.22 (d, 1H), 7.13 (d, 2H), 4.00 (s, 2H), 3.92 (s, 3H). MS (ESI) 317 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-67c362d7d8234513aa5b88fc8168c706
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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