1-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one → tert-Butyl 3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)carbonylamino)propanoate

HRID 2175231Notes

Reaction equation

HRID 2175231 reaction equation
CC1C(C)=CC=CC=1OCCCC(N1[C:19]2[C:14](=[C:15]([B:20]3[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]3)[CH:16]=[CH:17][CH:18]=2)CCC1)=O.BrC1C=CC=C2C=1CCCN2C(=O)CCCOC1C=CC=C(C)C=1C.BrC1C=C(C=CC=1)[CH2:63][O:64][C:65]([NH:67][CH2:68][CH2:69][C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])=[O:66]>>[CH3:26][C:23]1([CH3:25])[C:22]([CH3:27])([CH3:28])[O:21][B:20]([C:15]2[CH:14]=[C:19]([CH:18]=[CH:17][CH:16]=2)[CH2:63][O:64][C:65]([NH:67][CH2:68][CH2:69][C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])=[O:66])[O:24]1

Participants

4

Reactant 3

HCID 709817961-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneHCID 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 70982800tert-Butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate

Product 1

HCID 70984253tert-Butyl 3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)carbonylamino)propanoate

Procedure

The title compound was prepared using a procedure analogous to 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 except that 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one was replaced with tert-butyl 3-((3-bromobenzyloxy)carbonylamino)propanoate. LCMS, [M+Na]+=428.2.

Sources & evidence

ORD record
ord-0dd792f3d6364c3fac23d8f3f6e8dc66
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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