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

HRID 227769Notes

Reaction equation

HRID 227769 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-1-H-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 Mg2SO44, 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. customdried with Mg2SO44
  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-3a099ac59a244146a49765361f454939
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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