Methyl 4-bromopicolinate → 2-(2,3-Dimethylphenoxy)ethyl 5-(3-((3-tert-butoxy-3-oxopropylcarbamoyloxy)methyl)phenyl)-3,4-dihydroquinoline-1 (2H)-carboxylate

HRID 2175232Notes

Reaction equation

HRID 2175232 reaction equation
CC1C(C)=CC=CC=1OCCCC(N1C2C(=C(C3C=CN=C(C(OC)=O)C=3)C=CC=2)CCC1)=O.CC1C(C)=CC=CC=1OCCCC(N1C2C(=C(B3OC(C)(C)C(C)(C)O3)C=CC=2)CCC1)=O.CC1(C)C(C)(C)OB([C:76]2[CH:77]=[C:78]([CH:93]=[CH:94][CH:95]=2)[CH2:79][O:80][C:81]([NH:83][CH2:84][CH2:85][C:86]([O:88][C:89]([CH3:92])([CH3:91])[CH3:90])=[O:87])=[O:82])O1.BrC1C=CN=C(C(OC)=O)C=1.Br[C:109]1[CH:118]=[CH:117][CH:116]=[C:115]2[C:110]=1[CH2:111][CH2:112][CH2:113][N:114]2[C:119]([O:121][CH2:122][CH2:123][O:124][C:125]1[CH:130]=[CH:129][CH:128]=[C:127]([CH3:131])[C:126]=1[CH3:132])=[O:120]>>[C:89]([O:88][C:86](=[O:87])[CH2:85][CH2:84][NH:83][C:81]([O:80][CH2:79][C:78]1[CH:77]=[C:76]([C:109]2[CH:118]=[CH:117][CH:116]=[C:115]3[C:110]=2[CH2:111][CH2:112][CH2:113][N:114]3[C:119]([O:121][CH2:122][CH2:123][O:124][C:125]2[CH:130]=[CH:129][CH:128]=[C:127]([CH3:131])[C:126]=2[CH3:132])=[O:120])[CH:95]=[CH:94][CH:93]=1)=[O:82])([CH3:90])([CH3:91])[CH3:92]

Participants

6

Reactant 5

HCID 12828947Methyl 4-bromopicolinateHCID 709820304-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-oneHCID 70982851Methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinateHCID 709828952-(2,3-Dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylateHCID 70984253tert-Butyl 3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)carbonylamino)propanoate

Product 1

HCID 709825352-(2,3-Dimethylphenoxy)ethyl 5-(3-((3-tert-butoxy-3-oxopropylcarbamoyloxy)methyl)phenyl)-3,4-dihydroquinoline-1 (2H)-carboxylate

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 4-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one was replaced by tert-butyl 3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)carbonylamino)propanoate, and methyl 4-bromopicolinate was replaced by 2-(2,3-dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylate. LCMS, [M-tBu+2H]+=547.2. 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=8.1 Hz, 1H), 7.46-7.35 (m, 2H), 7.34-7.27 (m, 1H), 7.27-7.20 (m, 1H), 7.16 (t, J=7.9 Hz, 1H), 7.03 (t, J=7.9 Hz, 1H), 6.97 (d, J=7.5 Hz, 1H), 6.79 (d, J=7.7 Hz, 1H), 6.70 (d, J=8.1 Hz, 1H), 5.12 (s, 2H), 4.60-4.52 (m, 2H), 4.24-4.19 (m, 2H), 3.73 (t, J=6.4 Hz, 2H), 3.41 (dd, J=12.0, 6.0 Hz, 2H), 2.57 (t, J=6.3 Hz, 2H), 2.44 (t, J=5.9 Hz, 2H), 2.26 (s, 3H), 2.17 (s, 3H), 1.86-1.75 (m, 2H), 1.42 (s, 9H).

Sources & evidence

ORD record
ord-d8001805c9f54c539b47fe753fcd36b2
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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