4-(Hydroxymethyl)benzeneboronic acid → tert-Butyl 3-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)benzylcarbamate

HRID 2175255Notes

Reaction equation

HRID 2175255 reaction equation
[CH3:1][C:2]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15](C3C=CC(CO)=CC=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].OCC1C=CC(B(O)O)=CC=1.Br[C:45]1[CH:46]=[N:47][N:48]([CH2:50][C:51]2[CH:52]=[C:53]([CH:63]=[CH:64][CH:65]=2)[CH2:54][NH:55][C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[CH:49]=1>>[CH3:1][C:2]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:45]3[CH:46]=[N:47][N:48]([CH2:50][C:51]4[CH:52]=[C:53]([CH:63]=[CH:64][CH:65]=4)[CH2:54][NH:55][C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])[CH:49]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 3

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 709818684-(2,3-Dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-oneHCID 70982704tert-Butyl 3-((4-bromo-1H-pyrazol-1-yl)methyl)benzylcarbamate

Product 1

HCID 86712583tert-Butyl 3-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)benzylcarbamate

Procedure

The title compound was prepared using a procedure analogous to 4-(2,3-dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one except that 4-(hydroxymethyl)phenylboronic acid was replaced with tert-butyl 3-((4-bromo-1H-pyrazol-1-yl)methyl)benzylcarbamate. LCMS, [M+H]+=609.4.

Sources & evidence

ORD record
ord-2cb3d83130784ca89a02f0c4bfab4c10
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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