Ethyl Acetate → HCID 89924274, compound

HRID 1505689Notes

Reaction equation

HRID 1505689 reaction equation
[K].[CH3:2][C:3]([OH:6])([CH3:5])[CH3:4].[I:7][C:8]1[CH:9]=[N:10][N:11]([CH:13]2[CH2:18]CC(=O)C[CH2:14]2)[CH:12]=1.[Cl-].C[S+](C)(C)=O.CCOC(C)=O>CS(C)=O>[I:7][C:8]1[CH:9]=[N:10][N:11]([CH:13]2[CH2:18][CH2:5][C:3]3([O:6][CH2:4]3)[CH2:2][CH2:14]2)[CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 197819Trimethyloxosulphonium chlorideHCID 595411654-(4-iodo-1H-pyrazol-1-yl)cyclohexanoneHCID 86639980Potassium tert-butoxide

Product 1

HCID 89924274HCID 89924274, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Methyl-propan-2-ol potassium (466 mg; 4.15 mmol; 1.2 eq.) was added in one portion to a solution of 4-(4-Iodo-pyrazol-1-yl)-cyclohexanone (1.02 g; 3.50 mmol; 1.0 eq.) and trimethylsulfoxonium chloride (531 mg; 4.13 mmol; 1.2 eq.) in DMSO (50 mL). The reaction mixture was stirred at RT for 16 h. It was then poured into EtOAc. Organic phase was separated and washed with brine (three times), dried over magnesium sulfate, filtered and concentrated to give the title compound a white solid (813 mg, 76%). 1H NMR (300 MHz, DMSO) δ 8.01 (d, J=0.5 Hz, 1H), 7.52 (d, J=0.5 Hz, 1H), 4.41-4.26 (m, 1H), 2.66 (s, 2H), 2.13-1.85 (m, 6H), 1.34-1.21 (m, 2H). MS (ESI+): 305.1.

Workup

  1. customOrganic phase was separated
  2. washwashed with brine (three times)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ef57d318d444dbabc1ffc6d0b0a6a5c
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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