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

HRID 418619

반응식

HRID 418619 반응식
[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]

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 58790204HCID 58790204, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-26a0d89881f54a529dcf7ee37579dcca
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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