3-Bromobenzyl alcohol → 2-(4-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)-2-methylpropyl 4-nitrophenyl carbonate

HRID 2175263Notes

Reaction equation

HRID 2175263 reaction equation
[C:1](=[O:21])([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=CC=C(Br)[CH:5]=1.BrC1C=C(CO)C=CC=1.[CH3:31][C:32]1[C:63]([CH3:64])=[CH:62][CH:61]=[CH:60][C:33]=1[O:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]1[C:49]2[C:44](=[C:45]([C:50]3[CH:51]=[N:52][N:53](C(C)(C)CO)[CH:54]=3)[CH:46]=[CH:47][CH:48]=2)[CH2:43][CH2:42][CH2:41]1)=[O:39]>>[C:1](=[O:21])([O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)[O:2][CH2:3][C:4]([N:52]1[CH:51]=[C:50]([C:45]2[CH:46]=[CH:47][CH:48]=[C:49]3[C:44]=2[CH2:43][CH2:42][CH2:41][N:40]3[C:38](=[O:39])[CH2:37][CH2:36][CH2:35][O:34][C:33]2[CH:60]=[CH:61][CH:62]=[C:63]([CH3:64])[C:32]=2[CH3:31])[CH:54]=[N:53]1)([CH3:5])[CH3:9]

Participants

4

Reactant 3

HCID 851413-Bromobenzyl alcoholHCID 709831174-(2,3-dimethylphenoxy)-1-(5-(1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-oneHCID 867125803-Bromobenzyl 4-nitrophenyl carbonate

Product 1

HCID 867125882-(4-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)-2-methylpropyl 4-nitrophenyl carbonate

Procedure

The title compound was prepared using a procedure analogous to 3-bromobenzyl 4-nitrophenyl carbonate except that (3-bromophenyl)methanol was replaced with 4-(2,3-dimethylphenoxy)-1-(5-(1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one. LCMS, [M+H]+=627.5.

Sources & evidence

ORD record
ord-08acaf1bb3314c2daf8109629a60ceff
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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