Potassium Carbonate → 7-(1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridin-6-yl)-1H-indazol-3-amine

HRID 241959Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][N:20]=[C:19]3[NH2:23])[N:11]=[C:10]2[N:24]([CH3:27])[N:25]=[CH:26][C:9]=12.[CH3:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>CN(C=O)C>[CH3:27][N:24]1[C:10]2=[N:11][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:22]=3[NH:21][N:20]=[C:19]4[NH2:23])=[CH:13][C:8]([O:38][C:35]3[CH:34]=[CH:33][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:37][CH:36]=3)=[C:9]2[CH:26]=[N:25]1

Participants

Conditions

Temperature: 155 °C

Procedure

Potassium carbonate (0.14 g, 1.04 mmol) was added to a solution of 7-(4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-1H-indazol-3-amine 16 (0.30 g, 0.1046 mmol) and 4-methylsulfonyl phenol 8a (0.036 g, 0.2 mmol) in 2 mL DMF. Nitrogen was bubbled through the solution. The reaction mixture was heated in a microwave at 155° C. for 40 minutes. The crude compound was purified by mass directed purification to obtain 20 mg, 40% of 105 as a yellow solid. 1H NMR (400 MHz, DMSO) δ 11.53 (s, 1H), 8.21-7.64 (m, 6H), 7.64-7.40 (m, 3H), 7.40-6.91 (m, 1H), 5.51 (s, 2H), 4.12 (m, 3H), 3.21 (m, 3H). MS (ESI) m/z 435.1 (M+1)+

Workup

customNitrogen was bubbled through the solution
customThe crude compound was purified by mass
custompurification

Sources & evidence

ORD record: ord-a73809814f7d4333a716b271626afc9b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

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