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Water → 3-bromo-5-(2,6-difluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-indazole

HRID 1529349
Notes
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Reaction equation

HRID 1529349 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[F:18])[CH:9]=2)[NH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1.O>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]([F:18])=[CH:13][CH:14]=[CH:15][C:16]=3[F:17])[CH:9]=2)[N:4]([CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][O:30]2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 178505717HCID 178505717, compound

Product 1

HCID 679597623-bromo-5-(2,6-difluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-indazoleYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-bromo-5-(2,6-difluoro-phenyl)-1H-indazole (30.0 g, 97.05 mmol) and p-toluene sulfonic acid (3.7 g, 19.4 mmol) in THF (776 ml) was added 3,4-dihydro-2H-pyran (18.2 ml, 194.1 mmol) at RT. The mixture was stirred at 70° C. for 8 h. The reaction mixture was cooled to RT. Water was added to the reaction mixture and extracted with EtOAc (2×200 ml). The organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure. The crude product was purified by column using (100-200 mesh) silica with 0-5% EtOAc in hexane to provide 3-bromo-5-(2,6-difluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-indazole (18.5 g, 48.4% yield). MS (ESI, pos. ion) m/z: 393.1 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (2×200 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customThe crude product was purified by column

Sources & evidence

ORD record
ord-024bd6964e43472886e9d9b2e98695ff
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090593B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes