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

HRID 2361035Notes

Reaction equation

HRID 2361035 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-cbffe1339e2c4712a84584c75d459f4e
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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