4-Iodopyridine → HCID 78105635, compound

HRID 1777447Notes

Reaction equation

HRID 1777447 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].I[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>>[OH:3][C:1]([C:4]1[S:8][C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)=[CH:6][CH:5]=1)([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6094924-IodopyridineHCID 86680487HCID 86680487, compound

Product 1

HCID 78105635HCID 78105635, compoundYield 21.3%

Procedure

Using 5-(5-acetylthiophen-2-yl)-1-methylpyridin-2(1H)-one (0.07 g, 0.3 mmol), 4-iodopyridine (0.12 g, 0.6 mmol), and the procedure described for example 7 and step 4, crude compound was obtained and further purified by preparative TLC (5% methanol in dichloromethane) to give 5-(5-(1-hydroxy-1-(pyridin-4-yl)ethyl)thiophen-2-yl)-1-methylpyridin-2(1H)-one as off-white solid (0.02 g, 21% yield) in 99.8% HPLC purity. 1H NMR (400 MHz, DMSO-d6): δ 8.48 (d, 2H), 7.97 (d, 1H), 7.65 (dd, 1H), 7.45-7.44 (t, 2H), 7.07 (d, 1H), 6.94 (d, 1H), 6.41-6.38 (m, 2H), 3.42 (s, 3H), 1.85 (s, 3H); LC-MS m/z calculated for [M+H]+ 313.09. found 313.1.

Workup

  1. customcrude compound was obtained
  2. customfurther purified by preparative TLC (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d83c8558384341f4a1f37dbf86788914
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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