1-Chloro-4-iodobutane → 6-Chloro-2-(6-chloropyridin-3-yl)hexanoic acid

HRID 1803191Notes

Reaction equation

HRID 1803191 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26]I>>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 581101616-Chloro-2-(6-chloropyridin-3-yl)hexanoic acidYield 51.1%

Procedure

Step AJ (1): 2-(6-Chloropyridin-3-yl)acetic acid (2.5 g, 14.57 mmol) was deprotonated with NaHMDS (1.0 M in THF, 29.1 mL, 29.1 mmol) and reacted with 1-chloro-4-iodobutane (1.78 mL, 14.6 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(6-chloropyridine-3-yl)hexanoic acid (1.95 g, 51% yield). LC-MS (M−H)− 262.04.

Sources & evidence

ORD record
ord-a66bd0d19e004a9e8a5d94e9cc862026
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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