5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → Methyl 1-isopropyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-indazole-4-carboxylate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]2[C:6](C)=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]3[CH:35]=[CH:34][NH:33][C:30]3=[N:31][CH:32]=2)O1>>[CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([C:27]3[CH:28]=[C:29]4[CH:35]=[CH:34][NH:33][C:30]4=[N:31][CH:32]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]=2[CH:6]=[N:7]1)([CH3:12])[CH3:13]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
The title compound was prepared in the same manner as described for example 35 (step a) from methyl 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylate (1 g, 3.36 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.98 g, 4.04 mmol) wherein the reaction mixture was stirred at 100° C. for 5 h. The product was collected as an off white solid (600 mg, 53%). LCMS (ES−) m/z: 333.08.
Workup
- customThe product was collected as an off white solid (600 mg, 53%)
Sources & evidence
- ORD record
- ord-1f62eb6f9a164d15845f2aa07e9cdb72
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018382B2
Reaction notes
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