4-Bromopyridine-2-carboxylic acid → HCID 470750, compound

HRID 724956Notes

Reaction equation

HRID 724956 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([C:19]#[CH:20])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.Br[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([OH:32])=[O:31])[CH:25]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:24]4[CH:29]=[CH:28][N:27]=[C:26]([C:30]([OH:32])=[O:31])[CH:25]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 7351504-Bromopyridine-2-carboxylic acidHCID 10567137HCID 10567137, compound

Product 1

HCID 470750HCID 470750, compoundYield 34.9%

Procedure

By a procedure analogous to that described in Example 51b, 2-chloro-5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.83 g, 2.64 mmol) was coupled with 4-bromopicolinic acid (prepared by potassium permanganate oxidation of 4-bromo-2-picoline) (0.53 g, 2.62 mmol). The product was hydrogenated according to the procedure described in Example 3b to provide 0.4 g of the title compound as a mixture containing the corresponding des-chloro analog.

Sources & evidence

ORD record
ord-cfaad48bb71545538f45ae6f12dfe59e
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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