3-Bromoquinolin-6-ol → 2-(3-bromo-6-quinolinyloxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide

HRID 2222305Notes

Reaction equation

HRID 2222305 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.Br[CH:14]([CH2:27][CH3:28])[C:15]([NH:17][C:18]([CH3:26])([CH3:25])[C:19]#[C:20][CH2:21][CH2:22][CH2:23][Cl:24])=[O:16]>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:14]([CH2:27][CH3:28])[C:15]([NH:17][C:18]([CH3:26])([CH3:25])[C:19]#[C:20][CH2:21][CH2:22][CH2:23][Cl:24])=[O:16])=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 148078713-Bromoquinolin-6-olHCID 86602730HCID 86602730, compound

Product 1

HCID 692548132-(3-bromo-6-quinolinyloxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide

Procedure

In a similar procedure to Example 6 Stage 2, 3-bromo-6-hydroxyquinoline was reacted with 2-bromo-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide to give 2-(3-bromo-6-quinolinyloxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide as a colourless oil. 1H NMR (CDCl3) δ: 1.04-1.10(3H, t); 1.60(6H, s); 1.86-1.94(2H, m); 2.00-2.06(2H, m); 2.32-2.36(2H, t); 3.60-3.64(2H, t); 4.56(1H, t); 6.34(1H, s); 7.02 (1H, m); 7.42-7.46(1H, dd); 8.03 (1H, d); 8.22(1H, s); 8.78(1H, s).

Sources & evidence

ORD record
ord-f05c1ce0b0ac428aa0ebd987bc9cdb25
Source dataset
uspto-grants-2008_05
Patent number
US07371764B2

Reaction notes

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