Azido(trimethyl)stannane → HCID 66986312, compound

HRID 1254061Notes

Reaction equation

HRID 1254061 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:12]([CH3:22])[C:13]=2[S:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1)#[N:2].[N:29]([Sn](C)(C)C)=[N+:30]=[N-:31]>C1(C)C(C)=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:14][C:13]2[N:12]([CH3:22])[C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:10][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([C:1]3[N:29]=[N:30][NH:31][N:2]=3)=[CH:8][CH:7]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 44552858HCID 44552858, compound

Product 1

HCID 66986312HCID 66986312, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2-{4-(4-cyanophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 23, 160 mg, 0.41 mmol) and azidotrimethyltin (420 mg, 2.0 mmol) in xylene (1.5 mL) was heated at 140° C. under nitrogen for 2 hrs. After cooling, the reaction mixture was filtered through a pad of Celite and silica, and the filtrate was concentrated to afford 2-{5-[(4-Chlorophenyl)thio]-1-methyl-4-[4-(2H-tetrazol-5-yl)phenyl]-1H-imidazol-2-yl}pyridine, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered through a pad of Celite and silica
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f53a5db034864d1aaa86327f285c8c75
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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