Phosphorous triiodide → HCID 86658386, compound

HRID 455683Notes

Reaction equation

HRID 455683 reaction equation
IP(I)I.[Br:5][C:6]1[CH:7]=[C:8]2[C:18](=[CH:19][CH:20]=1)[O:17][C:11]1[CH:12]=[N:13][C:14]([Cl:16])=[CH:15][C:10]=1[C:9]2([CH2:22][O:23][CH:24]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:25][N+:26]([O-])=O)[NH2:21]>C(Cl)Cl>[NH2:21][C:9]1([CH2:22][O:23][CH:24]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:25]#[N:26])[C:10]2[CH:15]=[C:14]([Cl:16])[N:13]=[CH:12][C:11]=2[O:17][C:18]2[C:8]1=[CH:7][C:6]([Br:5])=[CH:20][CH:19]=2

Participants

4

Reactant 2

HCID 83485Phosphorous triiodideHCID 58465881HCID 58465881, compound

Product 1

HCID 86658386HCID 86658386, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TEA (1.263 ml, 9.06 mmol) and triiodophosphine (1.243 g, 3.02 mmol) were added to 7-bromo-3-chloro-5-((1-cyclohexyl-2-nitroethoxy)methyl)-5H-chromeno[2,3-c]pyridin-5-amine (1.5 g, 3.02 mmol) in DCM (30.2 ml) at 0° C. The reaction was stirred 10 minutes before the ice water bath was removed and the reaction was allowed to come to RT. After 1.5 hours, the solution is cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate, diluted with water, and extracted with DCM. The combined organic extracts were washed with 1N NaOH, water, saturated aqueous NaCl, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:4 EtOAc in hexane, to provide 2-((5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methoxy)-2-cyclohexylacetonitrile, [M+H]=462.0.

Workup

  1. customwas removed
  2. customto come to RT
  3. customquenched with saturated aqueous sodium bicarbonate
  4. additiondiluted with water
  5. extractionextracted with DCM
  6. washThe combined organic extracts were washed with 1N NaOH, water, saturated aqueous NaCl
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo
  10. customto give the crude material
  11. customThe crude material was purified by silica gel chromatography
  12. washby eluting with 1:4 EtOAc in hexane

Sources & evidence

ORD record
ord-141ce87fdfa34f18b6d2bca8f9dac8f9
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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