Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate → t-Butyl 4-(2-(2-bromo-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yl oxy)ethyl)piperazine-1-carboxylate

HRID 331308Notes

Reaction equation

HRID 331308 reaction equation
[Br:1][C:2]1[C:3](=[O:20])[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]([OH:19])[CH:5]=2.BrC1C(=O)C2C(C=1C1C=CC=CC=1)=CC=C(O)C=2.O[CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1>>[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:12]=[C:13]([F:18])[CH:14]=[C:15]([F:17])[CH:16]=1)=[CH:8][CH:7]=[C:6]([O:19][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])[CH2:44][CH2:43]1)[CH:5]=2

Participants

4

Reactant 3

HCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703160432-Bromo-3-(3,5-difluorophenyl)-6-hydroxy-1H-inden-1-one

Product 1

HCID 70314964t-Butyl 4-(2-(2-bromo-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yl oxy)ethyl)piperazine-1-carboxylate

Procedure

The procedure of Step 6 of Example 1 was repeated except for using 2-bromo-3-(3,5-difluorophenyl)-6-hydroxy-1H-inden-1-one obtained in Step 5 of Example 36 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, t-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate instead of 4-(2-hydroxyethyl)morpholine, being stirred for 4 d, and being purified by silica gel column chromatography (EtOAc/hexanes=1:4) to obtain the title compound.

Workup

  1. custombeing purified by silica gel column chromatography (EtOAc/hexanes=1:4)

Sources & evidence

ORD record
ord-441d054402c7462294e3c64431865092
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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