(Pyrimidin-5-yl)boronic acid → HCID 49803714, compound

HRID 1020397Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3Br)[C:18]2=[O:27])=[CH:12][CH:11]=1.NC1C=CC=CC=1NC(=O)C1C=CC(CN2CC3C(=CC(OC)=C(OC)C=3Br)C2=O)=CC=1.B(O)(O)[C:62]1[CH:67]=[N:66][CH:65]=[N:64][CH:63]=1>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[C:62]3[CH:63]=[N:64][CH:65]=[N:66][CH:67]=3)[C:18]2=[O:27])=[CH:12][CH:11]=1

Participants

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acid

HCID 49803415HCID 49803415, compound

HCID 49803713HCID 49803713, compound

Product 1

HCID 49803714HCID 49803714, compoundYield 68%

Procedure

The procedure of Example 2 was repeated except for using N-(2-aminophenyl)-4-((4-bromo-1-oxoisoindolin-2-yl)methyl)benzamide in Example 9 instead of N-(2-aminophenyl)-4-((4-bromo-5,6-dimethoxy-1-oxoisoindolin-2-yl)methyl)benzamide, and pyrimidin-5-yl-5-boronic acid instead of phenyl boronic acid to obtain the title compound (68%).

Sources & evidence

ORD record: ord-e41a2a8e274a4a18bd7bb9bb85238d0f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716326B2

Reaction notes

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