2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → 5-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-2-cyclopropylisoindolin-1-one

HRID 1778792Notes

Reaction equation

HRID 1778792 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10](I)[C:5]2=[CH:4][CH:3]=1.[CH:18]1([N:21]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26](B4OC(C)(C)C(C)(C)O4)[CH:27]=3)[C:22]2=[O:39])[CH2:20][CH2:19]1>>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([C:26]3[CH:27]=[C:28]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:39])[N:21]([CH:18]3[CH2:20][CH2:19]3)[CH2:29]4)[C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 594023502-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 867228676-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 867228725-[6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-2-cyclopropylisoindolin-1-one

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 72, Step 3 starting from 6-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine (Example 72, Step 2) and 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one. LCMS (M+H)+=409.1.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-f36cddcc1fb44fde83ade327e899fa6b
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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