1,3-Dichloro-2-fluoro-5-nitrobenzene → 4-(2,6-dichloro-4-nitrophenoxy)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

HRID 2241204노트

반응식

HRID 2241204 반응식
[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]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24]([Cl:31])[C:23]=1F>>[Cl:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24]([Cl:31])[C:23]=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

참가 물질

3

반응물 2

HCID 765541,3-Dichloro-2-fluoro-5-nitrobenzeneHCID 178490909HCID 178490909, 화합물

생성물 1

HCID 685169274-(2,6-dichloro-4-nitrophenoxy)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine수율 76.2%

실험 절차

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 1,3-dichloro-2-fluoro-5-nitrobenzene (0.117 g, 0.557 mmol), according to the procedure of Example 13, Step A. The crude product was purified Biotage 40S column eluting with 3:1 hexane/EtOAc then EtOAc to obtain the product (195 mg, 73%) as an off white solid. 1H NMR (CDCl3, 400 MHz) δ 8.37 (s, 1H), 8.29 (d, J=5.5 Hz, 1H), 7.37 (d, J=8.6 Hz, 2H), 6.85 (d, J=9.0 Hz, 2H), 5.93 (d, J=5.5 Hz, 1H), 5.58 (s, 2H), 3.77 (s, 3H), 2.75 (s, 3H). LRMS (esi pos) m/e 460 (M+1).

후처리

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

출처 및 근거

ORD 기록
ord-fe8c2c1d0c964b71aa09484257ef1f7b
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

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