Stannous Chloride → 4-(2-(4-(((2-Chloroethyl)(methyl)amino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 418619

Reaction equation

HRID 418619 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][C:24]=3[F:32])[CH:14]=2)=[CH:9][CH:8]=1)[CH3:5].Cl[Sn]Cl>CO>[Cl:1][CH2:2][CH2:3][N:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:24]=3[F:32])[CH:14]=2)=[CH:11][CH:12]=1)[CH3:5]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 58790204HCID 58790204, compound

Product 1

HCID 587901534-(2-(4-(((2-Chloroethyl)(methyl)amino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 86 (375 mg, 0.79 mmol) in MeOH (15 ml) was added SnCl2×2H2O (891 mg, 5, eq, 3.95 mmol) and the reaction mixture was heated to reflux for 3 hours. The mixture was cooled to RT and poured onto ice/water then basified to pH 9. The mixture was filtered and the aqueous solution was extracted with EtOAc and the EtOAc was washed with brine solution. The organic phase was collected, dried over Na2SO4, filtered and concentrated and the 4-(2-(4-(((2-chloroethyl)(methyl)amino)methyl)phe-nyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine (87) (348 mg, 100% yield) was used immediately in the next step with no additional purification.

Workup

  1. temperatureeq, 3.95 mmol) and the reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. additionpoured onto ice/water
  4. filtrationThe mixture was filtered
  5. extractionthe aqueous solution was extracted with EtOAc
  6. washthe EtOAc was washed with brine solution
  7. customThe organic phase was collected
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-26a0d89881f54a529dcf7ee37579dcca
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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