3-Nitrostyrene → 5-[(1E)-2-(3-Nitrophenyl)vinyl]-3-(4-fluorophenyl)-1H-indazole

HRID 1272783Notes

Reaction equation

HRID 1272783 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[CH2:25])([O-:20])=[O:19]>>[N+:18]([C:21]1[CH:22]=[C:23](/[CH:24]=[CH:25]/[C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][N:6]=[C:5]3[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:26]=[CH:27][CH:28]=1)([O-:20])=[O:19]

Participants

3

Reactant 2

HCID 685143-NitrostyreneHCID 224802935-bromo-3-(4-fluorophenyl)-1H-indazole

Product 1

HCID 224801845-[(1E)-2-(3-Nitrophenyl)vinyl]-3-(4-fluorophenyl)-1H-indazoleYield 52%

Procedure

The title compound (0.134 g, 52% yield) was prepared as described in Example 132 D, using 5-bromo-3-(4-fluorophenyl)-1H-indazole (0.291 g, 1.0 mmol) and 3-nitrostyrene (0.298 g, 2.0 mmol). 1H NMR (CDCl3) δ 10.12 (br s, 1H), 8.41 (t, 1H), 8.11 (ddd, 1H), 8.07 (s, 1H), 7.97 (m, 2H), 7.82 (d, 1H), 7.73 (dd, 1H), 7.54 (m, 2H), 7.40 (d, 1H), 7.26 (m, 2H), 7.16 (d, 1H); ES-MS (m/z) 360 [M+1]+.

Sources & evidence

ORD record
ord-7a314abf2dab4bcab0028b2626a25942
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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