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

HRID 1774825Notes

Reaction equation

HRID 1774825 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7](Br)[CH:8]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]3)O1>>[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]3)[CH:6]=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 229922643-(Aminomethyl)-5-bromopyridineHCID 591171873,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one

Product 1

HCID 866791766-(5-Aminomethyl-pyridin-3-yl)-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 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one (intermediate A-34) gave the title compound as a light yellow amorphous solid. MS: 254.4 (M+H+).

Sources & evidence

ORD record
ord-fd0794a060c345c6b29b593fffbd99e1
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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