Benzene, 1-fluoro-2-methyl-4-nitro- → 1-(4-methoxybenzyl)-3-methyl-4-(2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

HRID 2241206Notes

Reaction equation

HRID 2241206 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=3[C:10]([CH3:18])=[N:9]2)=[CH:5][CH:4]=1.F[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=1[CH3:31]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=4[CH3:31])=[C:11]3[C:10]([CH3:18])=[N:9]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 178490909HCID 178490909, compound

Product 1

HCID 685179271-(4-methoxybenzyl)-3-methyl-4-(2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridineYield 48%

Procedure

Prepared from 1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-ol (0.150 g, 0.557 mmol; prepared as in Example 5, Step B) and 1-fluoro-2-methyl-4-nitrobenzene (0.0864 g, 0.557 mmol) according to the procedure of Example 13, Step A. The crude product was purified by Biotage 40S column eluting with 3:1 hexane/EtOAc then EtOAc to obtain the product (107 mg, 48%) as a off white solid. 1H NMR (CDCl3, 400 MHz) δ 8.33 (d, J=5.5 Hz, 1H), 8.25 (m, 1H), 8.15 (m, 1H), 7.35 (d, J=8.6 Hz, 2H), 7.17 (d, J=9.0 Hz, 1H), 6.84 (d, J=8.6 Hz, 2H), 6.18 (d, J=5.5 Hz, 1H), 5.57 (s, 2H), 3.77 (s, 3H), 2.64 (s, 3H), 2.36 (s, 3H). LRMS (esi pos) m/e 405 (M+1).

Workup

  1. customThe crude product was purified by Biotage 40S column
  2. washeluting with 3:1 hexane/EtOAc

Sources & evidence

ORD record
ord-7c75d48423714c208cff6af8875c427e
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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