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

HRID 17119

Reaction equation

HRID 17119 reaction equation
[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.C1C(=O)N([I:31])C(=O)C1.O>CN(C=O)C>[I:31][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

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 184507633-(4-Phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

Product 1

HCID 184508787-Iodo-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 10A (1.69 g, 5.3 mmol) in DMF (20 mL) was treated with NIS (1.26 g, 5.6 mmol), stirred at room temperature for 3 hours, poured into water, and filtered. The filter cake was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes to provide 1.64 g (70% yield) of the desired product. MS (ESI(+)) m/e 444.8 (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe filter cake was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4913f3f3dcaf4671a8270d6e845f5975
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Linked notes

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