1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one → HCID 178481472, compound

HRID 1774743Notes

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]=[N:25][CH:26]=[C:27]([CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][C@H:31]2[C:35]([CH3:43])([CH3:42])[O:36][SiH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:28]=1>>[C:38]([SiH2:37][O:36][C:35]([CH3:43])([CH3:42])[C@@H:31]1[CH2:32][CH2:33][CH2:34][N:30]1[CH2:29][C:27]1[CH:28]=[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:24]=[N:25][CH:26]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

Reactant 2

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

HCID 178455462HCID 178455462, compound

Product 1

HCID 178481472HCID 178481472, 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 3-bromo-5-[(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-ylmethyl]-pyridine to give the title compound as an off white waxy solid. MS: 352.3 (M+H+).

Sources & evidence

ORD record: ord-4350526b66c047658c6f540e8d4ad944
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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