Azobisisobutyronitrile → tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

HRID 589406Notes

Reaction equation

HRID 589406 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>FC(C1C=CC=CC=1)(F)F>[Br:25][CH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 57370583Tert-butyl 3-methyl-1H-pyrazolo[3,4-B]pyridine-1-carboxylate

Product 1

HCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylateYield 8.3%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
75 °C

Procedure

tert-Butyl 3-methyl-1H-pyrazolo[3,4-b]pyridin-1-carboxylate (6.6 g, 28.3 mmol) was added into trifluoromethylbenzene (300 mL), and heated to 75° C. Then NBS (5.04 g, 28.3 mmol) was added, and after 15 minutes AIBN (465 mg, 2.8 mmol) was added, and heated to 80° C. and reacted for 1 hour. It was cooled slowly to room temperature and reacted for 12 hours. It was filtered to remove solid. The filtrate was rotate evaporated to dryness, and chromatographed on a column (PE:EA=25:1) to obtain a white solid 730 mg, at a yield of 8.3%.

Workup

  1. temperatureheated to 80° C.
  2. customreacted for 1 hour
  3. temperatureIt was cooled slowly to room temperature
  4. customreacted for 12 hours
  5. filtrationIt was filtered
  6. customto remove solid
  7. customThe filtrate was rotate evaporated to dryness
  8. customchromatographed on a column (PE:EA=25:1)

Sources & evidence

ORD record
ord-59f97e13af7b4750bab6089306b702db
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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