Dimethylformamide → (3-Cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester

HRID 930583Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10](I)=[N:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[C-]#N.[C-]#N.[Zn+2].O>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:19]#[N:20])=[N:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A 250 mL flask was charged with (3-iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester (15.0 g), PdCl2(dppf) (3.0 g), Zn(CN)2 (4.96 g), DMF (200 mL) and H2O (14 mL). The flask containing the resultant suspension was degassed and backfilled with nitrogen gas repeatedly for 5 minutes, followed by addition of Pd2(dba)3 (3.85 g) to the reaction mixture. The reaction mixture was heated under N2 at 90° C. for 16 h, cooled to room temperature, diluted with H2O (800 mL) and filtered. The collected solid was washed with toluene (10 mL) to provide (3-cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester as a yellow solid.

Workup

customwas degassed
additionfollowed by addition of Pd2(dba)3 (3.85 g) to the reaction mixture
temperaturecooled to room temperature
additiondiluted with H2O (800 mL)
filtrationfiltered
washThe collected solid was washed with toluene (10 mL)

Sources & evidence

ORD record: ord-c8330bb7d32345a5b6d80f87a1e3e912
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296740B2

Reaction notes

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