4-Aminophenol → 4-(3-(1-trityl-1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine

HRID 593944Notes

Reaction equation

HRID 593944 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:16]1[C:21]([C:22]2[CH:23]=[N:24][N:25]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:26]=2)=[CH:20][CH:19]=[CH:18][N:17]=1>CN1CCCC1=O>[C:27]([N:25]1[CH:26]=[C:22]([C:21]2[C:16]([O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:23]=[N:24]1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 866141632-chloro-3-(1-trityl-1H-pyrazol-4-yl)pyridine

Product 1

HCID 667318804-(3-(1-trityl-1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
20 °C

Procedure

In 4 separate microwave vessels were added equal amounts of the following (total/4): dissolved 4-aminophenol (0.054 g, 0.498 mmol) in 1-methyl-2-pyrrolidinone (4.7 mL), added cesium carbonate (0.309 g, 0.948 mmol). Each mixture was stirred at 20° C. for 5 minutes, after which was added 2-chloro-3-(1-trityl-1H-pyrazol-4-yl)pyridine (0.200 g, 0.474 mmol) and heated to 200° C. in the microwave for 6 minutes. The solutions were combined and extracted into EtOAc, washed 1×H2O, 1×NaCl, dried with Mg2SO4, filtered through fritted funnel, and concentrated. The crude residue was purified by silica gel chromatography using 25-70% EtOAc/Hexanes. The product fraction were concentrated to yield 4-(3-(1-trityl-1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine as brown oil. MS m/z=495 [M+1]+. Calc'd for C33H26N4O: 494.59.

Workup

  1. customIn 4 separate microwave vessels
  2. additionwere added equal amounts of the following (total/4)
  3. temperatureheated to 200° C. in the microwave for 6 minutes
  4. extractionextracted into EtOAc
  5. washwashed 1×H2O, 1×NaCl
  6. dry with materialdried with Mg2SO4
  7. filtrationfiltered through fritted funnel
  8. concentrationconcentrated
  9. customThe crude residue was purified by silica gel chromatography
  10. concentrationThe product fraction were concentrated

Sources & evidence

ORD record
ord-9f2b87e9beb54f598b34196a5dcc0928
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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