Tributyltin azide → HCID 178465001, compound

HRID 870038

Reaction equation

HRID 870038 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[CH3:11])=[O:8])=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH:3]=1.[N:28]([Sn](CCCC)(CCCC)CCCC)=[N+:29]=[N-:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[NH:30][N:29]=[N:28][N:19]=3)=[CH:16][CH:17]=2)[CH3:11])=[O:8])=[C:4]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 579009815-chloro-3-(3-chlorobenzyl)-N-[1-(4-cyanophenyl)ethyl]thiophene-2-carboxamide

Product 1

HCID 178465001HCID 178465001, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-chloro-3-(3-chlorobenzyl)-N-[1-(4-cyanophenyl)ethyl]thiophene-2-carboxamide from Example 2, Step 1 (192 mg, 0.462 mmol) and azidotributyltin (0.380 mL, 1.39 mmol) in toluene (1 mL) was heated to reflux under N2 for 3 h and cooled to r.t. The crude was purified directly by flash chromatography (2-10% iPrOH/hexanes) to give the desired product as a white solid. MS (−ESI): m/z 456 (M−1)−.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 3 h
  3. customThe crude was purified directly by flash chromatography (2-10% iPrOH/hexanes)

Sources & evidence

ORD record
ord-0430cb0c7c544db5858fada837921588
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Linked notes

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