Potassium Carbonate → 6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazole-3-carbonitrile

HRID 2203335Notes

Reaction equation

HRID 2203335 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]([F:28])([F:27])[C:21]([F:26])([F:25])[CH2:22][CH2:23]I>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[N:7][N:8]2[CH2:23][CH2:22][C:21]([F:26])([F:25])[C:20]([F:28])([F:27])[F:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1100921,1,1,2,2-Pentafluoro-4-iodobutaneHCID 534084026-Chloro-1H-indazole-3-carbonitrile

Product 1

HCID 866789726-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile solution (450 mL) containing the intermediate from Step C (30 g, 169 mmol), potassium carbonate (116.6 g, 844 mmol) and 1,1,1,2,2-pentafluoro-4-iodobutane (97.2 g, 354.7 mmol) was refluxed for 36 hours. The solution was cooled to room temperature and partitioned between EtOAc and water. The organic phase was concentrated and the crude material was filtered through a plug of silica gel using 10% EtOAc/heptanes as the eluent. The isolated material was subsequently recrystallized from heptanes to give the indicated product. 1H NMR (400 MHz, CH3 CN-d3): δ 7.87-7.80 (m, 2H); 7.40 (dd, J=8.7, 1.7 Hz, 1H); 4.77 (t, J=7.0 Hz, 2H); 2.95-2.78 (m, 2H). m/z=324.1 (M+H).

Workup

  1. temperaturewas refluxed for 36 hours
  2. custompartitioned between EtOAc and water
  3. concentrationThe organic phase was concentrated
  4. filtrationthe crude material was filtered through a plug of silica gel using 10% EtOAc/heptanes as the eluent
  5. customThe isolated material was subsequently recrystallized from heptanes
  6. customto give the indicated product

Sources & evidence

ORD record
ord-9e93c23440404453a04d7c33c7c4a5bd
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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