Tributyltin Chloride → HCID 178438781, compound

HRID 896691Notes

Reaction equation

HRID 896691 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH2:20][CH:21]([C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=4)[C:22]#[N:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].C([Sn](Cl)(CCCC)CCCC)CCC.[N-:48]=[N+:49]=[N-:50].[Na+]>C1(C)C(C)=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=4)[C:22]4[NH:50][N:49]=[N:48][N:23]=4)[CH:15]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 102045083-[3-(6-Isopropyl-quinolin-8-yl)-phenyl]-2-(4-methanesulfonyl-phenyl)-propionitrile

Product 1

HCID 178438781HCID 178438781, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
21 °C

Procedure

A solution of Example 78 (160 mg, 0.35 mmol), tri-n-butyltin chloride (0.478 mL, 1.76 mmol) and sodium azide (115 mg, 1.76 mmol) in xylene (5 mL) was heated at 150° C. for 18 h. Cooling to 21° C., then purification by flash chromatography (eluting with CH2Cl2/MeOH, NH4OH, 50:5:1) followed by stirring vigorously in ether for 1 h, then filtered, afforded the title compound as a white powder.

Workup

  1. custompurification
  2. washby flash chromatography (eluting with CH2Cl2/MeOH, NH4OH, 50:5:1)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-1421440d0a4d44bc90c266ad93da7a00
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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