3-(Aminomethyl)-5-bromopyridine → 6-(5-Aminomethyl-pyridin-3-yl)-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1774818Notes

Reaction equation

HRID 1774818 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7](Br)[CH:8]=1.[F:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][C:17](=[O:22])[N:18]2[CH3:21])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1>>[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[F:10])[N:18]([CH3:21])[C:17](=[O:22])[CH2:16][CH2:15]3)[CH:6]=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 229922643-(Aminomethyl)-5-bromopyridineHCID 86679131HCID 86679131, compound

Product 1

HCID 715336356-(5-Aminomethyl-pyridin-3-yl)-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

Procedure

In analogy to the procedure described for the preparation of example 45, reaction of 3-aminomethyl-5-bromopyridine and 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-22) gave the title compound as a light yellow solid. MS: 286.7 (M+H+).

Sources & evidence

ORD record
ord-883f6ae7565d41bda0d3c7c66207f527
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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