3-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole → 3-(2-Methoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

HRID 1020946Notes

Reaction equation

HRID 1020946 reaction equation
[O:1]([CH3:3])[K].CO.C1(C)C=CC=CC=1.F[C:14]1[CH:19]=[C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[CH:27]=3)[N:22]([C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:21]=2)[CH:17]=[CH:16][N:15]=1>>[CH3:3][O:1][C:14]1[CH:19]=[C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[CH:27]=3)[N:22]([C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:21]=2)[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 583719213-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazoleHCID 178501899HCID 178501899, compound

Product 1

HCID 673446273-(2-Methoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazoleYield 100%

Conditions

Temperature
70 °C

Procedure

In a 250 ml pressure vessel, 3-(2-Fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole 3BV (5.005 g, 10.0 mmole) was dissolved in 0.1N KOCH3/MeOH/Toluene (Acros, 150 mL, 15.0 mmole) under dry N2 gas. The pressure vessel was tightly sealed and heated under stirring at 70° 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 500 ml RBF and evaporated to dryness. The resulting solid was dissolved in CH2Cl2 and washed with saturated NaCl solution and dried over MgSO4. The solvent was evaporated to dryness and dried under high vacuum to yield 4BV as a brown solid (5.12 g, 100%).

Workup

  1. customThe pressure vessel was tightly sealed
  2. temperatureheated
  3. temperatureThe pressure vessel was cooled to 0° C. in ice-bath
  4. customevaporated to dryness
  5. dissolutionThe resulting solid was dissolved in CH2Cl2
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated to dryness
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-3ec114f409f8495abaa60812f278037e
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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