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

HRID 634471Notes

Reaction equation

HRID 634471 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.[NH2:37][C:38]1[N:43]=[CH:42][N:41]=[C:40]2[N:44]([CH:48]([C:50]3[O:51][C:52](=[O:67])[C:53]4[C:58]([C:59]=3[CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH3:49])[N:45]=[C:46](I)[C:39]=12.[F:68][C:69]1[CH:70]=[C:71](B(O)O)[CH:72]=[C:73]([OH:75])[CH:74]=1>>[NH2:37][C:38]1[N:43]=[CH:42][N:41]=[C:40]2[N:44]([CH:48]([C:50]3[O:51][C:52](=[O:67])[C:53]4[C:58]([C:59]=3[CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH3:49])[N:45]=[C:46]([C:71]3[CH:72]=[C:73]([OH:75])[CH:74]=[C:69]([F:68])[CH:70]=3)[C:39]=12

Participants

4

Reactant 3

HCID 447173083-Fluoro-5-hydroxybenzeneboronic acidHCID 1181313053-(1-(4-amino-3-(2-aminopyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-oneHCID 1181314763-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-benzyl-1H-isochromen-1-one

Product 1

HCID 1181311423-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-benzyl-1H-isochromen-1-oneYield 29.8%

Procedure

The title compound was made in a similar way as that of the compound of example 51 from 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-benzyl-1H-isochromen-1-one (Intermediate D15, 45 mg, 0.086 mmol), (3-fluoro-5-hydroxyphenyl)boronic acid (26.8 mg, 0.172 mmol), to give the title compound (13 mg, 19.8%) as brown pale solid.

Sources & evidence

ORD record
ord-bbb2a0e7c0d449bfbd50f37c06cc333a
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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