Acetic Acid → HCID 58465881, compound

HRID 455682Notes

Reaction equation

HRID 455682 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1([CH2:24][OH:25])[C:21]2[CH:20]=[C:19]([Cl:22])[N:18]=[CH:17][C:16]=2[O:15][C:14]2[C:9]1=[CH:10][C:11]([Br:23])=[CH:12][CH:13]=2.[N+:26](/[CH:29]=[CH:30]/[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([O-:28])=[O:27].C(O)(=O)C>C1COCC1.[Cl-].[NH4+].O.CCOC(C)=O>[Br:23][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[O:15][C:16]1[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][C:21]=1[C:8]2([CH2:24][O:25][CH:30]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:29][N+:26]([O-:28])=[O:27])[NH2:7]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 11094860132839-80-6HCID 23665647Potassium tert-butoxideHCID 58465926HCID 58465926, compound2×

Product 1

HCID 58465881HCID 58465881, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Potassium t-butoxide (0.517 g, 4.61 mmol) was added in one portion to a solution of (5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (Intermediate X, 1.5 g, 4.39 mmol) in THF (30 mL) at −78° C. After stirring for 45 minutes, (E)-(2-nitrovinyl)cyclohexane (0.716 g, 4.61 mmol) in THF (15.00 mL) was added slowly via syringe. The reaction was stirred at −78° C. for 20 minutes and was quenched with acetic acid (0.502 mL, 8.78 mmol) at −78° C., diluted with saturated aqueous ammonium chloride, water and EtOAc. After warming to RT, the layers were seperated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, saturated aqueous sodium chloride, 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 1:6 to 1:4 EtOAc in hexane, to provide 7-bromo-3-chloro-5-((1-cyclohexyl-2-nitroethoxy)methyl)-5H-chromeno[2,3-c]pyridin-5-amine as a yellow oil. [M+H]+=496.1.

Workup

  1. stirringThe reaction was stirred at −78° C. for 20 minutes
  2. customthe layers were seperated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic extracts were washed with water, saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material
  9. customThe crude material was purified by silica gel chromatography
  10. washby eluting with 1:6 to 1:4 EtOAc in hexane

Sources & evidence

ORD record
ord-5df1ee26405148ffbdd8bbb297e61310
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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