Methyl 4-bromopicolinate → 4-(2,3-Dimethylphenoxy)-1-(5-(1-(3-(2-hydroxyethoxy)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

HRID 2175289Notes

Reaction equation

HRID 2175289 reaction equation
[CH3:1][C:2]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15](C3C=CN=C(C(OC)=O)C=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].BrC1C=CN=C(C(OC)=O)C=1.C([O:49][CH2:50][CH2:51][O:52][C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([CH2:59][N:60]2[CH:64]=[C:63](Br)[CH:62]=[N:61]2)[CH:54]=1)(=O)C>>[CH3:1][C:2]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:63]3[CH:62]=[N:61][N:60]([CH2:59][C:55]4[CH:56]=[CH:57][CH:58]=[C:53]([O:52][CH2:51][CH2:50][OH:49])[CH:54]=4)[CH:64]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 3

HCID 12828947Methyl 4-bromopicolinateHCID 709828132-(3-((4-Bromo-1H-pyrazol-1-yl)methyl)phenoxy)ethyl acetateHCID 70982851Methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinate

Product 1

HCID 709826674-(2,3-Dimethylphenoxy)-1-(5-(1-(3-(2-hydroxyethoxy)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

Procedure

The title compound was prepared using a procedure analogous to methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinate except that methyl 4-bromopicolinate was replaced with 2-(3-((4-bromo-1H-pyrazol-1-yl)methyl)phenoxy)ethyl acetate. LCMS, [M+H]+=540.4.

Sources & evidence

ORD record
ord-c40ff2af606c4855a34d57544e5ab5de
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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