4-Iodopyridine → HCID 71544295, compound

HRID 2406449Notes

Reaction equation

HRID 2406449 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8]([C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)(=[O:10])[CH3:9]>>[OH:10][C:8]([C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

3

Reactant 2

HCID 6094924-IodopyridineHCID 86680485HCID 86680485, compound

Product 1

HCID 71544295HCID 71544295, compoundYield 18.4%

Procedure

Using 4-iodo pyridine (0.22 g, 1.076 mmol), and 6′-acetyl-[3,3′-bipyridine]-6-carbonitrile (0.12 g, 0.54 mmol) and procedure described for example 7 and step 4, crude product was obtained. The crude product was purified by preparative TLC (5% methanol in ethyl acetate) to obtain 6′-(1-hydroxy-1-(pyridin-4-yl)ethyl)-[3,3′-bipyridine]-6-carbonitrile as off-white solid (30 mg, 18% yield) in 98% HPLC purity. 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.94 (s, 1H), 8.46 (d, 2H), 8.38 (dd, 1H), 8.23 (dd, 1H), 8.14 (d, 1H), 7.82 (d, 1H), 7.49 (d, 2H), 6.27 (s, 1H), 1.9 (s, 3H); LC-MS m/z calculated for [M+H]+ 303.12, found 303.1.

Workup

  1. customcrude product was obtained
  2. customThe crude product was purified by preparative TLC (5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-ff033ec832224079a028e1df95ccdc7a
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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