2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole → 2-{4-[(4-bromo-1H-imidazol-1-yl)methyl]-3-methoxyphenyl}-1,3-benzoxazole

HRID 7745

Reaction equation

HRID 7745 reaction equation
COC1C=C(C2OC3C=CC=CC=3N=2)C=CC=1CN1C=CN=N1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][C:34]3[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=3[N:36]=2)=[CH:28][C:27]=1[O:41][CH3:42].[Br:43][C:44]1[N:45]=[CH:46][NH:47][CH:48]=1>>[Br:43][C:44]1[N:45]=[CH:46][N:47]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[O:33][C:34]4[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=4[N:36]=3)=[CH:28][C:27]=2[O:41][CH3:42])[CH:48]=1

Participants

4

Reactant 3

HCID 101718252-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazoleHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazoleHCID 178418934HCID 178418934, compound

Product 1

HCID 101505362-{4-[(4-bromo-1H-imidazol-1-yl)methyl]-3-methoxyphenyl}-1,3-benzoxazole

Procedure

Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 4-bromo-1H-imidazole (150 mg, 1.0 mmol) afforded the desired 2-{4-[(4-bromo-1H-imidazol-1-yl)methyl]-3-methoxyphenyl}-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.94–7.99 (m, 3H), 7.85–7.87 (m, 1H), 7.75–7.78 (m, 1H), 7.65–7.68 (m, 1H), 7.43–7.49 (m, 2H), 7.20 (s, 1H), 5.55 (s, 2H), 4.09 (s, 3H). MS (ESI) 384 (M+H)+.

Sources & evidence

ORD record
ord-be02f65dc25f4d68a537d777c24187ef
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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