(Pyrimidin-5-yl)boronic acid → HCID 51002368, compound

HRID 331277Notes

Reaction equation

HRID 331277 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)=[C:15](Br)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[N:54]1[CH:59]=[C:58](B(O)O)[CH:57]=[N:56][CH:55]=1>>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)=[C:15]([C:58]4[CH:59]=[N:54][CH:55]=[N:56][CH:57]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703123176-(2-Morpholino ethoxy)-2-bromo-3-(4-chlorophenyl)-1H-inden-1-one

Product 1

HCID 51002368HCID 51002368, compoundYield 71%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 6-(2-morpholinoethoxy)-2-bromo-3-(4-chlorophenyl)-1H-inden-1-one obtained in Step 6 of Example 28 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, 5-pyrimidinylboronic acid instead of 3-pyridinylboronic acid, and being purified by silica gel column chromatography (acetone/hexanes=2:3) to obtain the title compound (71%).

Workup

  1. custombeing purified by silica gel column chromatography (acetone/hexanes=2:3)

Sources & evidence

ORD record
ord-994f0f9b507d45cbb0d41bddccd54f02
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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