N-Iodosuccinimide → 7-Iodo-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

HRID 17140

반응식

HRID 17140 반응식
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]3[C:19]([NH2:23])=[N:20][CH:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]N1C(=O)CCC1=O>CN(C=O)C>[I:24][C:22]1[C:17]2[S:16][CH:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:13][CH:12]=3)[C:18]=2[C:19]([NH2:23])=[N:20][CH:21]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 184507633-(4-Phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

생성물 1

HCID 184508787-Iodo-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of Example 219B (5 g, 15.7 mmol) in DMF (100 mL) was treated with N-iodosuccinimide (4.23 g, 18.8 mmol), stirred at ambient temperature for 2 hours, concentrated to half the original volume, and poured into 5% sodium thiosulfate (400 mL). The mixture was filtered and the filter cake was washed with water and dried. The solids were dissolved in dichloromethane (300 mL), treated with silica gel (80 g), and concentrated. The residue was transferred to a silica gel column (600 g) and chromatographed with ethyl acetate/heptane (1:6) to provide 5.2 g (75%) of the desired product. 1H NMR (CD2Cl2, 400 MHz) δ 7.95 (s, 1H), 7.33-7.29 (m, 4H), 7.12 (s, 1H), 7.10 (t, 1H), 7.02-6.99 (m, 4H), 4.76 (br s, 1H); 13C NMR (CD2Cl2, 400 MHz) δ 158.4, 156.8, 154.7, 154.4, 148.6, 138.4, 131.3, 131.2, 130.4, 124.4, 122.9, 120.0, 119,9, 118.8, 72.0.

후처리

  1. concentrationconcentrated to half the original volume
  2. additionpoured into 5% sodium thiosulfate (400 mL)
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with water
  5. customdried
  6. dissolutionThe solids were dissolved in dichloromethane (300 mL)
  7. additiontreated with silica gel (80 g)
  8. concentrationconcentrated
  9. customchromatographed with ethyl acetate/heptane (1:6)

출처 및 근거

ORD 기록
ord-dff3e8914e1642b09fc7349c0c1f1600
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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