3-Fluoro-5-hydroxybenzeneboronic acid → 4-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1H-isochromen-1-one

HRID 634469Notes

Reaction equation

NC1N=CN=C2N(C(C3OC(=O)C4C(C=3C3C=CC=CC=3)=CC=CC=4)C)N=C(C3C=NC(N)=NC=3)C=12.[C:37]([N:40]1[CH2:45][CH:44]=[C:43]([C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:49](=[O:56])[O:48][C:47]=2[CH:57]([N:59]2[C:63]3=[N:64][CH:65]=[N:66][C:67]([NH2:68])=[C:62]3[C:61](I)=[N:60]2)[CH3:58])[CH2:42][CH2:41]1)(=[O:39])[CH3:38].[F:70][C:71]1[CH:72]=[C:73](B(O)O)[CH:74]=[C:75]([OH:77])[CH:76]=1>>[C:37]([N:40]1[CH2:45][CH:44]=[C:43]([C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:49](=[O:56])[O:48][C:47]=2[CH:57]([N:59]2[C:63]3=[N:64][CH:65]=[N:66][C:67]([NH2:68])=[C:62]3[C:61]([C:73]3[CH:74]=[C:75]([OH:77])[CH:76]=[C:71]([F:70])[CH:72]=3)=[N:60]2)[CH3:58])[CH2:42][CH2:41]1)(=[O:39])[CH3:38]

Participants

Reactant 3

HCID 447173083-Fluoro-5-hydroxybenzeneboronic acid

HCID 1181310774-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1H-isochromen-1-one

HCID 1181313053-(1-(4-amino-3-(2-aminopyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one

Product 1

HCID 1181312574-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1H-isochromen-1-oneYield 43.5%

Procedure

The title compound was mane in a similar way as that or the compound of example 51 from 4-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1H-isochromen-1-one (Intermediate D12, 1.08 g, 1.941 mmol), (3-fluoro-5-hydroxyphenyl)boronic acid (0.605 g, 3.88 mmol), to give the title compound (456 mg, 43.5%) as a pale grey solid.

Sources & evidence

ORD record: ord-e1dcb7d45969470897891a8462825b1d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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