Isopropyl iodide → HCID 60141761, compound

HRID 1805270Notes

Reaction equation

HRID 1805270 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][N:10]=1.[F-].[Cs+].I[CH:36]([CH3:38])[CH3:37]>C(#N)C.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH:36]([CH3:38])[CH3:37])=[O:15])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[C:21]=2[C:22]([F:24])([F:25])[F:23])[O:11][N:10]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 25953Cesium fluorideHCID 86668508HCID 86668508, compound

Product 1

HCID 60141761HCID 60141761, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid (30 mg, 0.064 mmol), cesium fluoride (12 mg, 0.077 mmol) and 2-iodopropane (0.008 mL, 0.077 mmol) were dissolved in dried acetonitrile (1 mL) and the mixture was refluxed for 20 h. The mixture was diluted with dichloromethane and washed with water. The organic phase was dried over Na2SO4, filtered and the solvent was solvent removed under reduced pressure. The product was purified by pTLC (PE/EE 9/1) to give 26 mg of a yellow oil (yield 79%). Result of LC/MS [M+H]+: 511.8; 1H NMR (CDCl3): 1.02 (6H, d, 2×CH3), 5.02 (1H, m, CH-propyl), 7.18 (1H, t, CH-arom.), 7.28-7.61 (6H m, CH-arom.), 8.31 (1H, s, CH-pyraz.).

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customremoved under reduced pressure
  6. customThe product was purified by pTLC (PE/EE 9/1)

Sources & evidence

ORD record
ord-ea1d791db4be47b5bbca9ac52fbf775f
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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