1-Methyl-2-(tributylstannyl)-1H-imidazole → N-(2-(1-methyl-1H-imidazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide

HRID 1519972Notes

Reaction equation

HRID 1519972 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[NH:7][C:8](=[O:20])[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[CH3:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[Sn](CCCC)(CCCC)CCCC>>[CH3:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[NH:7][C:8](=[O:20])[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 27632521-Methyl-2-(tributylstannyl)-1H-imidazoleHCID 68754386N-(2-iodothiophen-3-yl)-2-(naphthalen-1-yl)acetamide

Product 1

HCID 59636663N-(2-(1-methyl-1H-imidazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide

Procedure

This molecule was synthesized from N-(2-iodothiophen-3-yl)-2-(naphthalen-1-yl)acetamide and 1-methyl-2-(tributylstannyl)-1H-imidazole according to protocol E. The residue was directly purified by HPLC to yield N-(2-(1-methyl-1H-imidazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide. Method [7] Retention time 3.41 min by HPLC (MH+ 348). 1H NMR (300 MHz, CDCl3) δ 10.27 (s, 1H), 7.87 (m, 3H), 7.51 (m, 6H), 6.91 (d, J=1.5 hz, 1H), 6.82 (d, J=1.5 Hz, 1H), 4.15 (s, 3H), 3.68 (s, 2H).

Workup

  1. customThe residue was directly purified by HPLC

Sources & evidence

ORD record
ord-18def5e3b7994a1a84a0da7bb46acb87
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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