1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one → HCID 178481473, compound

HRID 1774746Notes

Reaction equation

HRID 1774746 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8](B3OC(C)(C)C(C)(C)O3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:21].Br[C:23]1[CH:24]=[C:25]([CH2:29][N:30]2[C@H:34]([C:35]([CH3:43])([CH3:42])[O:36][SiH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:33][CH2:32][C:31]2=[O:44])[CH:26]=[N:27][CH:28]=1>>[C:38]([SiH2:37][O:36][C:35]([CH3:43])([CH3:42])[C@@H:34]1[CH2:33][CH2:32][C:31](=[O:44])[N:30]1[CH2:29][C:25]1[CH:24]=[C:23]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:21])[CH2:4][CH2:5]3)[CH:28]=[N:27][CH:26]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 137329755HCID 137329755, compound

Product 1

HCID 178481473HCID 178481473, compound

Procedure

In analogy to the procedure described for the preparation of intermediate A-3 [C], 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) has been coupled to (S)-1-(5-bromo-pyridin-3-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one to give the title compound as a brown foam. MS: 480.3 (M+H+).

Sources & evidence

ORD record
ord-693783e8728a4685b0a4cf1f6b9518c0
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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