Sodium Iodide → HCID 11533199, compound

HRID 2054174Notes

Reaction equation

HRID 2054174 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.[CH:18]1([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[CH:25]=2)=[O:22])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>CCOC(C)=O.CN(C)C=O>[CH:18]1([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH:31]3[CH2:32][CH2:33][N:34]([CH2:2][C:3]4[CH:8]=[CH:7][C:6]([S:9]([C:11]5[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=5)=[O:10])=[CH:5][CH:4]=4)[CH2:35][CH2:36]3)[CH:25]=2)=[O:22])[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 69116061HCID 69116061, compoundHCID 86235737HCID 86235737, compound

Product 1

HCID 11533199HCID 11533199, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Into a vial was added 4-(bromomethyl)-1-[(4-methylphenyl)sulfinyl]benzene (100 mg, 0.320 mmol), cyclopropyl-N-(4-methyl-3-(4-piperidyl)phenyl)carboxamide (50.0 mg, 0.190 mmol), potassium carbonate (60.0 mg, 0.430 mmol), NaI (30.0 mg, 0.200 mmol) and 2.50 mL of dimethylformamide. The mixture was stirred for 2-3 min at 25° C. and heated to 90° C. (oil bath). After stirring 12 h at 90° C., the mixture was allowed to cool to 25° C. and was diluted with 50 mL of EtOAc. The reaction solution was then washed with water (3×30 mL) and the aqueous solution was extracted with 30 mL of EtOAc. The organic solutions were combined and dried over MgSO4. Removal of solvent in vacuo gave crude product that was purified by flash column chromatography (eluent: 97% EtOAc: 3% methanol (2 M ammonia)) to afford cyclopropyl-N-{4-methyl-3-[1-({4-[(4-methylphenyl)sulfinyl]phenyl}methyl)(4-piperidyl)]phenyl}carboxamide (36.0 mg, 39.1% yield). 1H NMR (CDCl3) δ 7.62 (s, 1H), 7.54-7.43 (m, 4H), 7.42-7.31 (m, 3H), 7.24-7.10 (m, 3H), 7.05-6.91 (m, 1H), 3.47 (s, 2H), 2.92-2.81 (m, 2H), 2.66-2.52 (m, 1H), 2.29 (s, 3H), 2.18 (s, 3H), 2.08-1.97 (m, 2H), 1.76-1.54 (m, 4H), 1.48-1.38 (m, 1H), 1.02-0.91 (m, 2H), 0.75-0.68 (m, 2H). ESMS m/e: 487.2 (M+H)+.

Workup

  1. temperatureheated to 90° C. (oil bath)
  2. stirringAfter stirring 12 h at 90° C.
  3. temperatureto cool to 25° C.
  4. washThe reaction solution was then washed with water (3×30 mL)
  5. extractionthe aqueous solution was extracted with 30 mL of EtOAc
  6. dry with materialdried over MgSO4
  7. customRemoval of solvent in vacuo
  8. customgave crude product that
  9. customwas purified by flash column chromatography (eluent: 97% EtOAc: 3% methanol (2 M ammonia))

Sources & evidence

ORD record
ord-5565a52c64834da69f443af7f6720a87
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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