(5-Fluoropyridin-3-yl)boronic acid → 4-(2-(6-(5-fluoropyridin-3-yl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)ethyl)phenol

HRID 1422484Notes

Reaction equation

HRID 1422484 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH:11]([CH3:13])[CH3:12])[N:9]=[CH:10][C:5]2=[C:4]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[N:3]=1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[N:29][CH:30]=1>>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[N:7]=[C:6]3[N:8]([CH:11]([CH3:13])[CH3:12])[N:9]=[CH:10][C:5]3=[C:4]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[N:3]=2)[CH:28]=[N:29][CH:30]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 866434614-(2-(6-chloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)ethyl)phenol

Product 1

HCID 594089034-(2-(6-(5-fluoropyridin-3-yl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)ethyl)phenol

Procedure

Following the procedure of Example 15d, 4-(2-(6-chloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)ethyl)phenol (b) was reacted with 5-fluoropyridin-3-ylboronic acid. The crude residue was purified by reverse-phase HPLC (C18 column, eluting with ACN—H2O 0.05% TFA) to afford the title compound as an off-white solid.

Workup

  1. customThe crude residue was purified by reverse-phase HPLC (C18 column, eluting with ACN—H2O 0.05% TFA)

Sources & evidence

ORD record
ord-862560c58b5e4274b693944763ce029e
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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