3,5-Dibromopyridine → HCID 137329756, compound

HRID 1774791Notes

Reaction equation

HRID 1774791 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:14])([CH3:13])[C@H:8]([NH2:12])[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20](Br)[CH:21]=1>>[Br:15][C:16]1[CH:21]=[C:20]([NH:12][C@@H:8]([C:7]([CH3:13])([CH3:14])[O:6][SiH2:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]([CH3:10])[CH3:11])[CH:19]=[N:18][CH:17]=1

Participants

3

Reactant 2

HCID 693693,5-DibromopyridineHCID 131734728HCID 131734728, compound

Product 1

HCID 137329756HCID 137329756, compound

Procedure

In analogy to the procedures described for the preparation of intermediate A-3 [B] and A-3 [C]: i) (R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propylamine has been reacted with 3,5-dibromopyridine to give (5-bromo-pyridin-3-yl)-[(R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amine; ii) subsequent condensation with 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) gave the title compound as light yellow amorphous solid. MS: 454.3 (M+H+).

Workup

  1. customIn analogy to the procedures described for the preparation of intermediate A-3 [B] and A-3 [C]

Sources & evidence

ORD record
ord-d2338681d9024b50a597dd8b56d16017
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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