Potassium tert-butoxide → 3-(2-Ethoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

HRID 1020950Notes

Reaction equation

HRID 1020950 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:39][C:40](C)([O-:42])C.[K+]>CCO>[CH2:40]([O:42][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1)[CH3:39]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 583719213-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

Product 1

HCID 673446593-(2-Ethoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a 150 mL pressure vessel, to the stirred solution of 3-(2-Fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole 3BV (2.0 g, 4.0 mmole) in anhydrous EtOH (40 mL), solid potassium tert-butoxide (12 g, 10.0 mmole) was added under dry N2 gas. The pressure vessel was tightly sealed and heated at 80° C. for 24 hours. The pressure vessel was cooled to 0° C. in ice-bath before opening. The contents of the pressure vessel were transferred to 250 mL RBF and concentrated to a small volume. The resulting mixture was partitioned between EtOAc and H2O. The organic phase was separated, washed with saturated NaCl solution and dried over MgSO4. The solvent was evaporated to dryness to give a crude solid 11BV (1.5 g, 71%).

Workup

  1. customThe pressure vessel was tightly sealed
  2. temperatureThe pressure vessel was cooled to 0° C. in ice-bath
  3. concentrationconcentrated to a small volume
  4. customThe resulting mixture was partitioned between EtOAc and H2O
  5. customThe organic phase was separated
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated to dryness
  9. customto give a crude solid 11BV (1.5 g, 71%)

Sources & evidence

ORD record
ord-6be5afdf538747fc84dfb3bf78e267f8
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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