(Pyrimidin-5-yl)boronic acid → HCID 70307959, compound

HRID 331290Notes

Reaction equation

HRID 331290 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]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[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:55]1[CH:60]=[C:59](B(O)O)[CH:58]=[N:57][CH:56]=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]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=4)=[C:15]([C:59]4[CH:60]=[N:55][CH:56]=[N:57][CH:58]=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 70313397HCID 70313397, compound

Product 1

HCID 70307959HCID 70307959, compoundYield 36%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 6-(2-morpholinoethoxy)-2-bromo-3-(3,5-difluorophenyl)-1H-inden-1-one obtained in Step 6 of Example 36 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 prep HPLC (CH3CN/H2O=7:3) to obtain the title compound (36%).

Workup

  1. custombeing purified by prep HPLC (CH3CN/H2O=7:3)

Sources & evidence

ORD record
ord-88fbbebbc15444389344dff7a6b6ca81
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

Loading…