1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one → HCID 178481474, compound

HRID 1774727Notes

Reaction equation

HRID 1774727 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]([N:29]2[CH2:33][CH2:32][CH2:31][C@@H:30]2[C:34]([CH3:42])([CH3:41])[O:35][SiH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:28]=1>>[C:37]([SiH2:36][O:35][C:34]([CH3:42])([CH3:41])[C@H:30]1[CH2:31][CH2:32][CH2:33][N:29]1[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)([CH3:40])([CH3:38])[CH3:39]

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 178455459HCID 178455459, compound

Product 1

HCID 178481474HCID 178481474, 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-[(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-pyridine to give the title compound as a white solid. MS: 452.1 (M+H+).

Sources & evidence

ORD record
ord-cb10ef57c35740b0a5e22247b9794f69
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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