Quinoline-3-boronic acid → t-Butyl 4-(3-(3-(3,5-difluorophenyl)-1-oxo-2-(quinolin-3-yl)-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate

HRID 331354Notes

Reaction equation

HRID 331354 reaction equation
Br[C:2]1[C:3](=[O:36])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[CH:8][CH:7]=[C:6]([O:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)[CH:5]=2.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[N:63]1[C:72]2[C:67](=[CH:68][CH:69]=[CH:70][CH:71]=2)[CH:66]=[C:65](B(O)O)[CH:64]=1>>[F:17][C:15]1[CH:16]=[C:11]([C:10]2[C:9]3[C:4](=[CH:5][C:6]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:27][CH2:28]4)=[CH:7][CH:8]=3)[C:3](=[O:36])[C:2]=2[C:65]2[CH:64]=[N:63][C:72]3[C:67]([CH:66]=2)=[CH:68][CH:69]=[CH:70][CH:71]=3)[CH:12]=[C:13]([F:18])[CH:14]=1

Participants

4

Reactant 3

HCID 2734663Quinoline-3-boronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 70311966HCID 70311966, compound

Product 1

HCID 70310450t-Butyl 4-(3-(3-(3,5-difluorophenyl)-1-oxo-2-(quinolin-3-yl)-1H-inden-6-yloxy)propyl)piperazine-1-carboxylateYield 39%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using t-butyl 4-(3-(2-bromo-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate obtained in Step 1 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, 3-quinolinylboronic acid instead of 3-pyridinylboronic acid, and being purified by silica gel column chromatography (EtOAc/hexanes=1:1) to obtain the title compound (39%).

Workup

  1. custombeing purified by silica gel column chromatography (EtOAc/hexanes=1:1)

Sources & evidence

ORD record
ord-c3732fa219464055bd8b8e2b0da0d00e
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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