5-bromo-1-methyl-3-nitro-1H-1,2,4-triazole → Methyl 2(s)-ethoxy-3-[4-(2-methyl-5-nitro-2h[1,2,4]triazol-3-yl)phenyl]propanoate

HRID 1864559Notes

Reaction equation

HRID 1864559 reaction equation
Br[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([N+:8]([O-:10])=[O:9])[N:3]=1.[CH2:11]([O:13][C@@H:14]([CH2:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])[CH3:12]>>[CH2:11]([O:13][C@@H:14]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]([CH3:7])[N:5]=[C:4]([N+:8]([O-:10])=[O:9])[N:3]=2)=[CH:22][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])[CH3:12]

Participants

3

Reactant 2

HCID 27720935-bromo-1-methyl-3-nitro-1H-1,2,4-triazoleHCID 67147872methyl 2(S)-ethoxy-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]propanoate

Product 1

HCID 67148279Methyl 2(s)-ethoxy-3-[4-(2-methyl-5-nitro-2h[1,2,4]triazol-3-yl)phenyl]propanoateYield 62%

Procedure

In a manner similar to that of Example 9(e), starting with 0.9 g (4.35 mmol) of 5-bromo-1-methyl-3-nitro-1H-[1,2,4]triazole and 1.9 g (6.5 mmol) of methyl 2(S)-ethoxy-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]propanoate, 0.9 g (62%) of methyl 2(S)-ethoxy-3-[4-(2-methyl-5-nitro-2H-[1,2,4]triazol-3-yl)phenyl]propanoate is obtained in the form of a white solid with a melting point of 119° C.

Sources & evidence

ORD record
ord-9b77a9b5a45246d78875477724bee5f0
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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