HCID 86679131, compound → (rac)-N-(4-(7-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamide

HRID 530356Notes

Reaction equation

HRID 530356 reaction equation
Br[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:4]=2[CH:5]=[N:6][CH:7]=1.[F:17][C:18]1[CH:27]=[C:26]2[C:21]([CH2:22][CH2:23][C:24](=[O:29])[N:25]2[CH3:28])=[CH:20][C:19]=1B1OC(C)(C)C(C)(C)O1>>[F:17][C:18]1[CH:27]=[C:26]2[C:21]([CH2:22][CH2:23][C:24](=[O:29])[N:25]2[CH3:28])=[CH:20][C:19]=1[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 86679131HCID 86679131, compoundHCID 89456129N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamide

Product 1

HCID 71536768(rac)-N-(4-(7-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamideYield 70%

Procedure

In analogy to the procedure described for the preparation of intermediate A-2 [E], (rac)-N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)ethanesulfonamide (intermediate A-6) was reacted with 7-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-9). The Suzuki coupling had to be repeated three times to give the to give the title compound as off-white solid in 70% yield. MS: 404.1 (M+H+).

Workup

  1. customto give the

Sources & evidence

ORD record
ord-68d161f849254e6785e848be3bb57019
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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