7-chloro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one → (rac)-Ethanesulfonic acid [4-(7-chloro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6,7,8-tetrahydro-isoquinolin-8-yl]-amide

HRID 530359Notes

Reaction equation

HRID 530359 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:24]1[C:33]2[CH2:32][CH2:31][CH2:30][CH:29]([NH:34][S:35]([CH2:38][CH3:39])(=[O:37])=[O:36])[C:28]=2[CH:27]=[N:26][CH:25]=1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[C:24]1[C:33]2[CH2:32][CH2:31][CH2:30][CH:29]([NH:34][S:35]([CH2:38][CH3:39])(=[O:37])=[O:36])[C:28]=2[CH:27]=[N:26][CH:25]=1

Participants

3

Reactant 2

HCID 866791877-chloro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-oneHCID 89458481N-(4-Bromo-5,6,7,8-tetrahydro-8-isoquinolinyl)ethanesulfonamide

Product 1

HCID 71537344(rac)-Ethanesulfonic acid [4-(7-chloro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6,7,8-tetrahydro-isoquinolin-8-yl]-amideYield 40%

Procedure

In analogy to the procedure described for the preparation of example 28, 7-chloro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-10) and (rac)-ethanesulfonic acid (4-bromo-5,6,7,8-tetrahydro-isoquinolin-8-yl)-amide (intermediate B-4) were used to give the title compound as a white solid in 40% yield. MS: 434.2 (M+H)+.

Sources & evidence

ORD record
ord-079599df01644f399727cbe3c05a904f
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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