3-Fluoro-4-methoxyphenylboronic acid → t-Butyl 4-(3-(2-(3-fluoro-4-methoxyphenyl)-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate

HRID 331359Notes

Reaction equation

HRID 331359 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.[F:63][C:64]1[CH:65]=[C:66](B(O)O)[CH:67]=[CH:68][C:69]=1[O:70][CH3:71]>>[F:63][C:64]1[CH:65]=[C:66]([C:2]2[C:3](=[O:36])[C:4]3[C:9]([C:10]=2[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[CH:8][CH:7]=[C:6]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:27][CH2:28]2)[CH:5]=3)[CH:67]=[CH:68][C:69]=1[O:70][CH3:71]

Participants

4

Reactant 3

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 70311966HCID 70311966, compound

Product 1

HCID 70313706t-Butyl 4-(3-(2-(3-fluoro-4-methoxyphenyl)-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate

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 of Example 104 as a starting material instead of 6-(2-morpholino ethoxy)-2-bromo-3-phenyl-1H-inden-1-one, 3-fluoro-4-methoxyphenylboronic acid instead of 3-pyridinylboronic acid, and being purified by silica gel column chromatography (EtOAc/hexanes=1:1) to obtain the title compound.

Workup

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

Sources & evidence

ORD record
ord-b7d1e84ba569472c8c19d1550f8bab5b
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

Loading…