4-Chloro-2-fluoro-5-nitrotoluene → 4-(5-chloro-2-methyl-4-nitrophenoxy)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

HRID 2241202Notes

Reaction equation

HRID 2241202 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.[Cl:21][C:22]1[CH:27]=[C:26](F)[C:25]([CH3:29])=[CH:24][C:23]=1[N+:30]([O-:32])=[O:31]>>[Cl:21][C:22]1[C:23]([N+:30]([O-:32])=[O:31])=[CH:24][C:25]([CH3:29])=[C:26]([CH:27]=1)[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=3)[N:9]=[C:10]([CH3:18])[C:11]=12

Participants

3

Reactant 2

HCID 875934-Chloro-2-fluoro-5-nitrotolueneHCID 178490909HCID 178490909, compound

Product 1

HCID 685121264-(5-chloro-2-methyl-4-nitrophenoxy)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridineYield 75.3%

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-chloro-5-fluoro-4-methyl-2-nitrobenzene (0.106 g, 0.557 mmol), according to the procedure of Example 13, Step A. Purified by Biotage 40S column eluting with 3:1 hexane/EtOAc then EtOAc to obtain the product (184 mg, 75%) as an off white solid. 1H NMR (CDCl3, 400 MHz) δ 8.36 (d, J=5.1 Hz, 1H), 7.95 (s, 1H), 7.35 (d, J=9.0 Hz, 1H), 7.21 (s, 1H), 6.84 (d, J=8.6 Hz, 1H), 6.23 (d, J=5.1 Hz, 1H), 5.58 (s, 1H), 3.77 (s, 3H), 2.63 (s, 3H), 2.31 (s, 3H). LRMS (APCI pos) m/e 439 (M+1).

Workup

  1. customPurified by Biotage 40S column
  2. washeluting with 3:1 hexane/EtOAc

Sources & evidence

ORD record
ord-73ece77aacbe4795bc476c715f6e6731
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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