Dichloromethane → HCID 52913256, compound

HRID 540779Notes

Reaction equation

HRID 540779 reaction equation
[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:6][C:5]([C:19]2[CH:20]=[C:21]([C:25]([NH:28][S:29]([CH2:32][C:33]([F:36])([F:35])[F:34])(=[O:31])=[O:30])([CH3:27])[CH3:26])[CH:22]=[CH:23][CH:24]=2)=[N:4]1)[CH3:2].C(Cl)Cl.C1C(=O)N([I:47])C(=O)C1>CCOC(C)=O>[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[C:6]([I:47])[C:5]([C:19]2[CH:20]=[C:21]([C:25]([NH:28][S:29]([CH2:32][C:33]([F:36])([F:34])[F:35])(=[O:30])=[O:31])([CH3:27])[CH3:26])[CH:22]=[CH:23][CH:24]=2)=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 52913370HCID 52913370, compound

Product 1

HCID 52913256HCID 52913256, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[2-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)propan-2-yl]-2,2,2-trifluoroethanesulfonamide (560 mg, 10.5 mmol) and DCM (6.97 mL) was cooled to 0° C., treated with NIS (706 mg, 3.14 mmol) in a single portion. The mixture was protected from light and allowed to warm to rt as it was stirred overnight. The reaction was diluted with EtOAc and washed with water 2×, sat. aq. NaHCO3, brine, dried (MgSO4) and concentrated to afford a white solid purified via MPLC, 25 g silica, 10-60% EtOAc in heptanes to afford a white solid: MS: cal'd 662 (MH+), exp 662 (MH+).

Workup

  1. washwashed with water 2×, sat. aq. NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a white solid
  5. custompurified via MPLC, 25 g silica, 10-60% EtOAc in heptanes
  6. customto afford a white solid

Sources & evidence

ORD record
ord-9fd21b08f5d34fc9b53936e653186a5d
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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