Phenylboronic Acid → 2-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-6-phenylimidazo[1,2-a]pyridine

HRID 322450Notes

Reaction equation

HRID 322450 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][N:22]4[CH:26]=[CH:25][N:24]=[CH:23]4)=[CH:15][CH:14]=3)[N:10]=2)[CH:7]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[N:22]1([CH2:21][CH2:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:7][N:6]4[CH:8]=3)=[CH:14][CH:15]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 220098516-Bromo-2-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]imidazo[1,2-a]pyridine

Product 1

HCID 220096202-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-6-phenylimidazo[1,2-a]pyridineYield 78%

Procedure

In substantially the same manner as in Working Example 135, 6-bromo-2-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]imidazo[1,2-a]pyridine was allowed to react with phenylboronic acid to give 2-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-6-phenylimidazo[1,2-a]pyridine. The yield was 78%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 106-107° C.

Sources & evidence

ORD record
ord-14277a6973f04f6da702a2b804d6db6d
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

Loading…