Isopropyl iodide → HCID 86639800, compound

HRID 1804837Notes

Reaction equation

HRID 1804837 reaction equation
[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[N:4][N:5]([CH2:8][C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([OH:23])[C:20]([Cl:24])=[CH:19][C:18]=3[Cl:25])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7].I[CH:31]([CH3:33])[CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[N:4][N:5]([CH2:8][C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([O:23][CH:31]([CH3:33])[CH3:32])[C:20]([Cl:24])=[CH:19][C:18]=3[Cl:25])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 86639799HCID 86639799, compound

Product 1

HCID 86639800HCID 86639800, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(1-(2,4-dichloro-5-hydroxyphenyl)piperidin-4-yl)ethanone (30 mg, 0.064 mmol) in anhydrous acetonitrile (1.5 mL) was treated with 2-iodopropane (0.019 mL, 0.191 mmol) and cesium carbonate (41.5 mg, 0.127 mmol) and the mixture stirred at 50° C. for 1 h. After this time, the mixture was concentrated on a rotary evaporator and the resultant residue was partitioned between water and EtOAc. The EtOAc phase was washed with brine, dried (MgSO4) and concentrated to give 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(1-(2,4-dichloro-5-isopropoxyphenyl)piperidin-4-yl)ethanone. LC-MS: 512.20, [M+H]; tR=2.30 min (method a).

Workup

  1. concentrationAfter this time, the mixture was concentrated on a rotary evaporator
  2. customthe resultant residue was partitioned between water and EtOAc
  3. washThe EtOAc phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c8f948935c44ab5968749d6e4b86eb8
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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