Pyrazole → 2-[3-methoxy-4-(1H-pyrazol-1-ylmethyl)phenyl]-1,3-benzoxazole

HRID 7744

Reaction equation

HRID 7744 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH:14]=[CH:13]N=[N:11]1.Br[CH2:25]C1C=CC(C2OC3C=CC=CC=3N=2)=CC=1OC.N1C=CC=N1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH:14]=[CH:13][CH:25]=[N:11]1

Participants

4

Reactant 3

HCID 1048PyrazoleHCID 101718252-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazoleHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Product 1

HCID 101255902-[3-methoxy-4-(1H-pyrazol-1-ylmethyl)phenyl]-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 pyrazole (70 mg, 1.0 mmol) afforded the desired 2-[3-methoxy-4-(1H-pyrazol-1-ylmethyl)phenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.60–7.91 (m, 7H), 7.38–7.41 (m, 2H), 6.54 (m, 1H), 5.81 (s, 2H), 4.11 (s, 3H). MS (ESI) 306 (M+H)+.

Sources & evidence

ORD record
ord-4461be6f64b94b51bfff28eea4a5d2be
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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