6-Chloro-4-(3-methoxy-phenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidine → 6-(1h-Indazol-4-yl)-4-(3-methoxyphenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidine

HRID 876914Notes

Reaction equation

HRID 876914 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[N:3]=1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](B2OC(C)(C)C(C)(C)O2)=[N:22]1>O>[NH:21]1[C:29]2[C:24](=[C:25]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=4)[N:3]=3)[CH:26]=[CH:27][CH:28]=2)[CH:23]=[N:22]1

Participants

4

Reactant 2

HCID 583459596-Chloro-4-(3-methoxy-phenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidineHCID 178431105HCID 178431105, compound

Product 1

HCID 441815856-(1h-Indazol-4-yl)-4-(3-methoxyphenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Chloro-4-(3-methoxy-phenoxy)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was reacted with indazole boronic acid pinacol ester in General Procedure A. Addition of water gave a solid which was purified by preparative HPLC to give 114. NMR: (CDCl3): 3.81 (s, 3H, CH3), 4.18 (s, 3H, CH3), 7.02-7.04 (m, 2H, 2×ArH), 7.09 (m, H, ArH), 7.44-7.52 (m, 2H, 2×ArH), 7.70 (d, H, ArH, J=9 Hz), 8.16 (s, H, ArH), 8.22 (d, H, ArH, J=6.9 Hz), 8.34 (s, H, ArH), 13.17 (sbr, H, NH). MS: (ESI+) MH+=373.24

Workup

  1. customgave a solid which
  2. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-0f2a3d0da99141f6a27aaebcf8702e7c
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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