5-Acetyl-N-(4-chloro-3-iodophenyl)thiophene-2-carboxamide → 5-acetyl-N-(4-chloro-3-(pyridin-2-yl)phenyl)thiophene-2-carboxamide

HRID 632974Notes

Reaction equation

HRID 632974 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14](I)[CH:13]=2)=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br-].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Zn+]>>[C:1]([C:4]1[S:8][C:7]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=3)[CH:13]=2)=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 668778965-Acetyl-N-(4-chloro-3-iodophenyl)thiophene-2-carboxamideHCID 178418723HCID 178418723, compound

Product 1

HCID 586149005-acetyl-N-(4-chloro-3-(pyridin-2-yl)phenyl)thiophene-2-carboxamide

Procedure

5-Acetyl-N-(4-chloro-3-iodophenyl)thiophene-2-carboxamide (202 mg, 0.5 mmol) was used in Procedure B with 2-pyridylzincbromide (2.5 mL, 1.25 mmol, 0.5 M in THF). Purified by silica gel chromatography (10-100% ethyl acetate/hexanes) to yield 5-acetyl-N-(4-chloro-3-(pyridin-2-yl)phenyl)thiophene-2-carboxamide as a yellow solid: TLC Rf=0.19 (50% ethyl acetate/hexanes); 1H NMR (CDCl3, 400 MHz) δ 8.96 (bs, 1H), 8.67 (d, 1H), 7.79 (dt, 1H), 7.68 (m, 3H), 7.61 (d, 1H), 7.58 (d, 1H), 7.37 (d, 1H), 7.32 (m, 1H), 2.58 (s, 3H); MS (Q1) 357.0 (M)+.

Workup

  1. customPurified by silica gel chromatography (10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1e0f21be41964a92b530f8c0587e4dac
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

Loading…