1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one → HCID 71533267, compound

HRID 1774790Notes

Reaction equation

HRID 1774790 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[CH2:34][O:35][CH3:36])[CH:28]=1>>[CH3:36][O:35][CH2:34][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

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 86679115HCID 86679115, compound

Product 1

HCID 71533267HCID 71533267, 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-methoxymethyl-pyrrolidin-1-yl)-pyridine (intermediate A-6) to give the title compound as a yellow oil. MS: 352.3 (M+H+).

Sources & evidence

ORD record
ord-93b1d2c77bc8494f93b6fb50a08ed687
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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