6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine → 6-(1H-indazol-4-yl)-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH: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>>[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]([NH: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]1Participants
3
Procedure
6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with indazole boronic acid pinacol ester using General Procedure A. Purification on silica yielded 122. NMR: (CDCl3): 3.88 (s, 3H, CH3), 4.19 (s, 3H, CH3), 6.88-6.91 (m, H, ArH), 7.16-7.18 (m, H, ArH), 7.31 (sbr, H, NH), 7.40 (t. H, ArH, J=8.1 Hz), 7.50 (s, H, ArH), 7.55 (t. H, ArH, J=4 Hz), 7.65 (d, H, ArH, J=8.3 Hz), 8.45 (d, H, ArH, J=7.49 Hz), 9.17 (s, H, ArH) 10.2 (sbr, H, NH). MS: (ESI+) MH+=372.25