2-Bromo-6-methylpyridine → 2-[3-Methoxy-4-(6-methylpyridin-2-yl)phenyl]-1,3-benzoxazole

HRID 7782

Reaction equation

HRID 7782 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])[CH:5]=[CH:4][CH:3]=1.[CH3:25]OC1C=C(C2OC3C=CC=CC=3N=2)C=CC=1B1OC(C)(C)C(C)(C)O1.BrC1C=CC=C(C)N=1>>[CH3:24][O:23][C:9]1[CH:10]=[C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:25])[N:7]=1

Participants

4

Reactant 3

HCID 792052-Bromo-6-methylpyridineHCID 103093892-[4-(6-Bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazoleHCID 219909862-[3-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole

Product 1

HCID 102864592-[3-Methoxy-4-(6-methylpyridin-2-yl)phenyl]-1,3-benzoxazole

Procedure

Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (200 mg, 0.57 mmol) was reacted with 2-bromo-6-methylpyridine (65 μL, 0.57 mmol) to afford the desired 2-[3-methoxy-4-(6-methylpyridin-2-yl)phenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.96–7.95 (m, 2H), 7.89 (s, 1H), 7.82–7.79 (m, 1H), 7.67–7.60 (m, 3H), 7.39–7.36 (m, 2H), 7.14–7.12 (m, 1H), 4.00 (s, 3H), 2.65 (s, 3H). MS (ESI) 317 (M+H)+.

Sources & evidence

ORD record
ord-bcecc2c35bdc40a1afdd5bd24e47bf43
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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